DD228247A5 - Verfahren zur herstellung von 2,6-bis-fluormethyl-dihydropyridin-3,5-dicarbonsaeureestern - Google Patents

Verfahren zur herstellung von 2,6-bis-fluormethyl-dihydropyridin-3,5-dicarbonsaeureestern Download PDF

Info

Publication number: DD228247A5
Authority: DD; German Democratic Republic
Prior art keywords: bis; trifluoromethyl; mol; diethyl; mixture
Prior art date: 1983-08-11

Application number

DD84275353A

Other languages

German (de)

English (en)

Inventor

Len F Lee

Original Assignee

Monsanto Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-08-11

Filing date

1984-08-10

Publication date

1985-10-09

1984-08-10 Application filed by Monsanto Co filed Critical Monsanto Co

1985-10-09 Publication of DD228247A5 publication Critical patent/DD228247A5/de

Links

238000002360 preparation method Methods 0.000 title claims abstract description 51
238000000034 method Methods 0.000 title claims abstract description 36
ABELIEPKVUTLDA-UHFFFAOYSA-N 2,6-bis(fluoromethyl)-1,2-dihydropyridine-3,5-dicarboxylic acid Chemical class FCC1NC(=C(C=C1C(=O)O)C(=O)O)CF ABELIEPKVUTLDA-UHFFFAOYSA-N 0.000 title 1
239000011541 reaction mixture Substances 0.000 claims description 41
-1 aralkoxyalkyl Chemical group 0.000 claims description 33
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 32
238000006243 chemical reaction Methods 0.000 claims description 28
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 16
TUDHHJQPQZFEIH-UHFFFAOYSA-N piperidine-4,4-diol Chemical compound OC1(O)CCNCC1 TUDHHJQPQZFEIH-UHFFFAOYSA-N 0.000 claims description 14
150000001299 aldehydes Chemical class 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 11
229910021529 ammonia Inorganic materials 0.000 claims description 11
OCJKUQIPRNZDTK-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-oxobutanoate Chemical group CCOC(=O)CC(=O)C(F)(F)F OCJKUQIPRNZDTK-UHFFFAOYSA-N 0.000 claims description 11
YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical group CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 claims description 10
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical group CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 9
239000012024 dehydrating agents‎ Substances 0.000 claims description 9
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
239000007795 chemical reaction product Substances 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
239000000908 ammonium hydroxide Substances 0.000 claims description 4
230000018044 dehydration Effects 0.000 claims description 4
238000006297 dehydration reaction Methods 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
LKMUBWWZTSZGGV-UHFFFAOYSA-N methyl 4,4,4-trifluoro-3-oxobutanoate Chemical compound COC(=O)CC(=O)C(F)(F)F LKMUBWWZTSZGGV-UHFFFAOYSA-N 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 30
230000002363 herbicidal effect Effects 0.000 abstract description 4
239000004480 active ingredient Substances 0.000 abstract description 3
CMWVSXYUVBJPGQ-UHFFFAOYSA-N 1-methyl-2h-pyridine-3,5-dicarboxylic acid Chemical class CN1CC(C(O)=O)=CC(C(O)=O)=C1 CMWVSXYUVBJPGQ-UHFFFAOYSA-N 0.000 abstract description 2
GCHZJYILSPLAGV-UHFFFAOYSA-N diethyl 4-ethyl-2,6-dihydroxy-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCOC(=O)C1C(CC)C(C(=O)OCC)C(O)(C(F)(F)F)NC1(O)C(F)(F)F GCHZJYILSPLAGV-UHFFFAOYSA-N 0.000 abstract description 2
GBGUVYKDIHJKJV-UHFFFAOYSA-N diethyl 4-pyridin-3-yl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1C1=CC=CN=C1 GBGUVYKDIHJKJV-UHFFFAOYSA-N 0.000 abstract description 2
SRBGWSXPYLIJDW-UHFFFAOYSA-N dimethyl 4-(2-methylpropyl)-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OC)C1CC(C)C SRBGWSXPYLIJDW-UHFFFAOYSA-N 0.000 abstract description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 85
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
239000000203 mixture Substances 0.000 description 55
239000000047 product Substances 0.000 description 55
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
239000000243 solution Substances 0.000 description 43
239000003921 oil Substances 0.000 description 38
238000004458 analytical method Methods 0.000 description 35
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 33
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
238000010992 reflux Methods 0.000 description 28
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 18
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
239000007787 solid Substances 0.000 description 14
238000003756 stirring Methods 0.000 description 14
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
239000002253 acid Substances 0.000 description 13
239000003480 eluent Substances 0.000 description 13
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
238000000023 Kugelrohr distillation Methods 0.000 description 12
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
239000000460 chlorine Substances 0.000 description 11
239000012043 crude product Substances 0.000 description 11
239000005457 ice water Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 8
239000003208 petroleum Substances 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
239000012258 stirred mixture Substances 0.000 description 8
241000196324 Embryophyta Species 0.000 description 7
235000011114 ammonium hydroxide Nutrition 0.000 description 7
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 7
239000012259 ether extract Substances 0.000 description 7
238000004128 high performance liquid chromatography Methods 0.000 description 7
150000003222 pyridines Chemical class 0.000 description 7
MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical compound C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 description 6
WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 6
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 6
229910052731 fluorine Inorganic materials 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
230000014759 maintenance of location Effects 0.000 description 6
239000012279 sodium borohydride Substances 0.000 description 6
229910000033 sodium borohydride Inorganic materials 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
244000062793 Sorghum vulgare Species 0.000 description 4
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000000284 extract Substances 0.000 description 4
125000001153 fluoro group Chemical group F* 0.000 description 4
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
235000019713 millet Nutrition 0.000 description 4
239000012071 phase Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
RDOAUPPSCNSYPM-UHFFFAOYSA-N 3,4-dihydropyridine Chemical class C1CC=NC=C1 RDOAUPPSCNSYPM-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000004009 herbicide Substances 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
239000013067 intermediate product Substances 0.000 description 3
238000005580 one pot reaction Methods 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
238000000746 purification Methods 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000007858 starting material Substances 0.000 description 3
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
240000002245 Acer pensylvanicum Species 0.000 description 2
235000006760 Acer pensylvanicum Nutrition 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 2
240000000275 Persicaria hydropiper Species 0.000 description 2
235000017337 Persicaria hydropiper Nutrition 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
244000067505 Xanthium strumarium Species 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
239000012267 brine Substances 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
CZYYZLCVCGMUQH-UHFFFAOYSA-N diethyl 2,6-dihydroxy-4-propan-2-yl-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCOC(=O)C1C(C(C)C)C(C(=O)OCC)C(O)(C(F)(F)F)NC1(O)C(F)(F)F CZYYZLCVCGMUQH-UHFFFAOYSA-N 0.000 description 2
AHPKRIKCUUDCAN-UHFFFAOYSA-N diethyl 4-(acetyloxymethyl)-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1COC(C)=O AHPKRIKCUUDCAN-UHFFFAOYSA-N 0.000 description 2
SULMYDAFNFRSPU-UHFFFAOYSA-N diethyl 4-(chloromethyl)-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1CCl SULMYDAFNFRSPU-UHFFFAOYSA-N 0.000 description 2
KXBVHDQIORQKDX-UHFFFAOYSA-N diethyl 4-(hydroxymethyl)-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1CO KXBVHDQIORQKDX-UHFFFAOYSA-N 0.000 description 2
WJVMOBVYYNTOGK-UHFFFAOYSA-N diethyl 4-(hydroxymethyl)-2,6-bis(trifluoromethyl)-3,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1C(CO)C(C(=O)OCC)=C(C(F)(F)F)N=C1C(F)(F)F WJVMOBVYYNTOGK-UHFFFAOYSA-N 0.000 description 2
JWSNWHPBQOECBT-UHFFFAOYSA-N diethyl 4-(phenylmethoxymethyl)-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1COCC1=CC=CC=C1 JWSNWHPBQOECBT-UHFFFAOYSA-N 0.000 description 2
WQIKIFYMKDAWBQ-UHFFFAOYSA-N diethyl 4-propan-2-yl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1C(C)C WQIKIFYMKDAWBQ-UHFFFAOYSA-N 0.000 description 2
RZTAMFZIAATZDJ-UHFFFAOYSA-N felodipine Chemical class CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-UHFFFAOYSA-N 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
VMVNZNXAVJHNDJ-UHFFFAOYSA-N methyl 2,2,2-trifluoroacetate Chemical compound COC(=O)C(F)(F)F VMVNZNXAVJHNDJ-UHFFFAOYSA-N 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000002689 soil Substances 0.000 description 2
238000009331 sowing Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
239000001893 (2R)-2-methylbutanal Substances 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
NCNSBFDGXBKAKB-UHFFFAOYSA-N (methylsulfanyl)acetaldehyde Chemical compound CSCC=O NCNSBFDGXBKAKB-UHFFFAOYSA-N 0.000 description 1
VCLSSIUDTNSANT-UHFFFAOYSA-N 1,4-dihydropyridine-3,5-dicarbonitrile Chemical class N#CC1=CNC=C(C#N)C1 VCLSSIUDTNSANT-UHFFFAOYSA-N 0.000 description 1
238000004293 19F NMR spectroscopy Methods 0.000 description 1
VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 description 1
AHHYEFQWMUXGFH-UHFFFAOYSA-N 2,3-dihydroxypiperidine-1,2-dicarboxylic acid Chemical compound OC1CCCN(C(O)=O)C1(O)C(O)=O AHHYEFQWMUXGFH-UHFFFAOYSA-N 0.000 description 1
FNOHUOPNBFVCAR-UHFFFAOYSA-N 2,6-dihydroxy-4-(phenylmethoxymethyl)-5-(trifluoromethoxycarbonyl)piperidine-3-carboxylic acid Chemical compound C1=CC=C(C=C1)COCC2C(C(NC(C2C(=O)OC(F)(F)F)O)O)C(=O)O FNOHUOPNBFVCAR-UHFFFAOYSA-N 0.000 description 1
WROHDQHHCINLIL-UHFFFAOYSA-N 2,6-dihydroxypiperidine-3,5-dicarboxylic acid Chemical class OC1NC(O)C(C(O)=O)CC1C(O)=O WROHDQHHCINLIL-UHFFFAOYSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
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XXWKBLJJTQQHJD-UHFFFAOYSA-N 3-(trifluoromethoxycarbonyl)-3,4-dihydropyridine-5-carboxylic acid Chemical compound C1C(C=NC=C1C(=O)O)C(=O)OC(F)(F)F XXWKBLJJTQQHJD-UHFFFAOYSA-N 0.000 description 1
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244000248416 Fagopyrum cymosum Species 0.000 description 1
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244000286695 Melinis minutiflora var. inermis Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
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240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
244000208734 Pisonia aculeata Species 0.000 description 1
235000010829 Prunus spinosa Nutrition 0.000 description 1
235000015503 Sorghum bicolor subsp. drummondii Nutrition 0.000 description 1
244000064817 Sorghum halepense var. sudanense Species 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 description 1
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235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
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XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
150000003931 anilides Chemical class 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
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125000004429 atom Chemical group 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
230000003385 bacteriostatic effect Effects 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000005997 bromomethyl group Chemical group 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229910000423 chromium oxide Inorganic materials 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
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125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
238000005796 dehydrofluorination reaction Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
125000006003 dichloroethyl group Chemical group 0.000 description 1
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ZXAWHLVKRUWHRY-UHFFFAOYSA-N diethyl 2,6-dihydroxy-4-(2-methylpropyl)-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCOC(=O)C1C(CC(C)C)C(C(=O)OCC)C(O)(C(F)(F)F)NC1(O)C(F)(F)F ZXAWHLVKRUWHRY-UHFFFAOYSA-N 0.000 description 1
DAYXOPHTLAIXNI-UHFFFAOYSA-N diethyl 2,6-dihydroxy-4-methyl-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCOC(=O)C1C(C)C(C(=O)OCC)C(O)(C(F)(F)F)NC1(O)C(F)(F)F DAYXOPHTLAIXNI-UHFFFAOYSA-N 0.000 description 1
UALBMALJKYZROX-UHFFFAOYSA-N diethyl 2,6-dihydroxy-4-phenyl-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCOC(=O)C1C(O)(C(F)(F)F)NC(C(F)(F)F)(O)C(C(=O)OCC)C1C1=CC=CC=C1 UALBMALJKYZROX-UHFFFAOYSA-N 0.000 description 1
OLVIWZURBFUPJK-UHFFFAOYSA-N diethyl 2,6-dihydroxy-4-propyl-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCCC1C(C(=O)OCC)C(O)(C(F)(F)F)NC(O)(C(F)(F)F)C1C(=O)OCC OLVIWZURBFUPJK-UHFFFAOYSA-N 0.000 description 1
FNOWBFBMMDXGRX-UHFFFAOYSA-N diethyl 2,6-dihydroxy-4-pyridin-4-yl-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCOC(=O)C1C(O)(C(F)(F)F)NC(C(F)(F)F)(O)C(C(=O)OCC)C1C1=CC=NC=C1 FNOWBFBMMDXGRX-UHFFFAOYSA-N 0.000 description 1
UXIKETQSQUSCFK-UHFFFAOYSA-N diethyl 2-(difluoromethyl)-4-propyl-6-(trifluoromethyl)pyridine-3,5-dicarboxylate Chemical compound CCCC1=C(C(=O)OCC)C(C(F)F)=NC(C(F)(F)F)=C1C(=O)OCC UXIKETQSQUSCFK-UHFFFAOYSA-N 0.000 description 1
BAGRCZJSEZFXCL-UHFFFAOYSA-N diethyl 4-(2,2-dimethylpropyl)-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1CC(C)(C)C BAGRCZJSEZFXCL-UHFFFAOYSA-N 0.000 description 1
JLFKCBKBSQKHAF-UHFFFAOYSA-N diethyl 4-(2-methylpropyl)-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1CC(C)C JLFKCBKBSQKHAF-UHFFFAOYSA-N 0.000 description 1
UYIDEVKPTRZDEE-UHFFFAOYSA-N diethyl 4-(2-methylpropyl)-2,6-bis(trifluoromethyl)pyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(CC(C)C)C(C(=O)OCC)=C(C(F)(F)F)N=C1C(F)(F)F UYIDEVKPTRZDEE-UHFFFAOYSA-N 0.000 description 1
LCAPVZPVUYNAKH-UHFFFAOYSA-N diethyl 4-(furan-2-yl)-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1C1=CC=CO1 LCAPVZPVUYNAKH-UHFFFAOYSA-N 0.000 description 1
CNHBXFCYMDBXDB-UHFFFAOYSA-N diethyl 4-(methylsulfanylmethyl)-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1CSC CNHBXFCYMDBXDB-UHFFFAOYSA-N 0.000 description 1
DDMNVAFAARHEKL-UHFFFAOYSA-N diethyl 4-(phenylmethoxymethyl)-2,6-bis(trifluoromethyl)-3,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)N=C(C(F)(F)F)C(C(=O)OCC)C1COCC1=CC=CC=C1 DDMNVAFAARHEKL-UHFFFAOYSA-N 0.000 description 1
IYDJVFUHPPOVRY-UHFFFAOYSA-N diethyl 4-benzyl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1CC1=CC=CC=C1 IYDJVFUHPPOVRY-UHFFFAOYSA-N 0.000 description 1
TYRVPNSAQVAPHA-UHFFFAOYSA-N diethyl 4-butyl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCCCC1C(C(=O)OCC)=C(C(F)(F)F)NC(C(F)(F)F)=C1C(=O)OCC TYRVPNSAQVAPHA-UHFFFAOYSA-N 0.000 description 1
VKQCVRVWEGGMOG-UHFFFAOYSA-N diethyl 4-butyl-2,6-dihydroxy-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCCCC1C(C(=O)OCC)C(O)(C(F)(F)F)NC(O)(C(F)(F)F)C1C(=O)OCC VKQCVRVWEGGMOG-UHFFFAOYSA-N 0.000 description 1
PCKIXHBSEWBXDI-UHFFFAOYSA-N diethyl 4-cyclohexyl-2,6-bis(difluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)F)NC(C(F)F)=C(C(=O)OCC)C1C1CCCCC1 PCKIXHBSEWBXDI-UHFFFAOYSA-N 0.000 description 1
YHDUORJKJINJHO-UHFFFAOYSA-N diethyl 4-cyclohexyl-2,6-bis(trifluoromethyl)-3,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)N=C(C(F)(F)F)C(C(=O)OCC)C1C1CCCCC1 YHDUORJKJINJHO-UHFFFAOYSA-N 0.000 description 1
CSEWMUDHDDARLJ-UHFFFAOYSA-N diethyl 4-cyclohexyl-2-(difluoromethyl)-6-(trifluoromethyl)pyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)OCC)=C1C1CCCCC1 CSEWMUDHDDARLJ-UHFFFAOYSA-N 0.000 description 1
NHVHQWRNMTYRHG-UHFFFAOYSA-N diethyl 4-ethyl-1,4-dihydroxy-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCOC(=O)C1C(C(F)(F)F)N(O)C(C(F)(F)F)C(C(=O)OCC)C1(O)CC NHVHQWRNMTYRHG-UHFFFAOYSA-N 0.000 description 1
LZYYOEITHIIOIO-UHFFFAOYSA-N diethyl 4-ethyl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1CC LZYYOEITHIIOIO-UHFFFAOYSA-N 0.000 description 1
ULRRJVGKMSKJCN-UHFFFAOYSA-N diethyl 4-ethyl-2,6-bis(trifluoromethyl)-3,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1C(CC)C(C(=O)OCC)=C(C(F)(F)F)N=C1C(F)(F)F ULRRJVGKMSKJCN-UHFFFAOYSA-N 0.000 description 1
SVZGVEJQQBGUEJ-UHFFFAOYSA-N diethyl 4-methyl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1C SVZGVEJQQBGUEJ-UHFFFAOYSA-N 0.000 description 1
YXFLRUNKYAFMMK-UHFFFAOYSA-N diethyl 4-phenyl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1C1=CC=CC=C1 YXFLRUNKYAFMMK-UHFFFAOYSA-N 0.000 description 1
QWQNEQHPTRNLPP-UHFFFAOYSA-N diethyl 4-propyl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCCC1C(C(=O)OCC)=C(C(F)(F)F)NC(C(F)(F)F)=C1C(=O)OCC QWQNEQHPTRNLPP-UHFFFAOYSA-N 0.000 description 1
FQALQSNVGLOOBM-UHFFFAOYSA-N diethyl 4-pyridin-4-yl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1C1=CC=NC=C1 FQALQSNVGLOOBM-UHFFFAOYSA-N 0.000 description 1
IAGQAFFFTYNLFV-UHFFFAOYSA-N diethyl 4-thiophen-2-yl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1C1=CC=CS1 IAGQAFFFTYNLFV-UHFFFAOYSA-N 0.000 description 1
125000006001 difluoroethyl group Chemical group 0.000 description 1
PFUCIJSSNLMBOU-UHFFFAOYSA-N dimethyl 2,6-dihydroxy-4-(2-methylpropyl)-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound COC(=O)C1C(CC(C)C)C(C(=O)OC)C(O)(C(F)(F)F)NC1(O)C(F)(F)F PFUCIJSSNLMBOU-UHFFFAOYSA-N 0.000 description 1
ZQOKGFJVSMHJSW-UHFFFAOYSA-N dimethyl 2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)pyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)OC)=C1CC(C)C ZQOKGFJVSMHJSW-UHFFFAOYSA-N 0.000 description 1
ATZOPPBTWMBSCX-UHFFFAOYSA-N dimethyl 4-(2-methylpropyl)-2,6-bis(trifluoromethyl)-1,2-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(CC(C)C)C(C(=O)OC)=C(C(F)(F)F)NC1C(F)(F)F ATZOPPBTWMBSCX-UHFFFAOYSA-N 0.000 description 1
BBHSZXSULXLTCA-UHFFFAOYSA-N dimethyl 6-(difluoromethyl)-4-(2-methylpropyl)-2-(trifluoromethyl)-1,2-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(CC(C)C)C(C(=O)OC)=C(C(F)F)NC1C(F)(F)F BBHSZXSULXLTCA-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
235000021186 dishes Nutrition 0.000 description 1
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AEXYGJRYLCZIJM-UHFFFAOYSA-N ethyl 3-amino-4-methylpent-2-enoate Chemical compound CCOC(=O)C=C(N)C(C)C AEXYGJRYLCZIJM-UHFFFAOYSA-N 0.000 description 1
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CBDPWKVOPADMJC-UHFFFAOYSA-N ethyl 4,4-difluoro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)C(F)F CBDPWKVOPADMJC-UHFFFAOYSA-N 0.000 description 1
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239000011487 hemp Substances 0.000 description 1
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208000021822 hypotensive Diseases 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000003999 initiator Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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239000011777 magnesium Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
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WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
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238000002156 mixing Methods 0.000 description 1
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SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
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239000007800 oxidant agent Substances 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000005359 phenoxyalkyl group Chemical group 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010926 purge Methods 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
GJAWHXHKYYXBSV-UHFFFAOYSA-L quinolinate(2-) Chemical compound [O-]C(=O)C1=CC=CN=C1C([O-])=O GJAWHXHKYYXBSV-UHFFFAOYSA-L 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000012056 semi-solid material Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
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239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Environmental Sciences (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Particle Accelerators (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Cephalosporin Compounds (AREA)
Confectionery (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD84275353A 1983-08-11 1984-08-10 Verfahren zur herstellung von 2,6-bis-fluormethyl-dihydropyridin-3,5-dicarbonsaeureestern DD228247A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US52228183A	1983-08-11	1983-08-11
US60202284A	1984-04-24	1984-04-24

Publications (1)

Publication Number	Publication Date
DD228247A5 true DD228247A5 (de)	1985-10-09

Family

ID=27060765

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84275353A DD228247A5 (de)	1983-08-11	1984-08-10	Verfahren zur herstellung von 2,6-bis-fluormethyl-dihydropyridin-3,5-dicarbonsaeureestern

Country Status (33)

Country	Link
EP (1)	EP0135491B1 (fr)
KR (2)	KR890000481B1 (fr)
AT (1)	ATE40262T1 (fr)
AU (1)	AU566077B2 (fr)
BG (1)	BG42832A3 (fr)
BR (1)	BR8404010A (fr)
CA (1)	CA1269383C (fr)
CS (1)	CS261875B2 (fr)
CY (1)	CY1425A (fr)
DD (1)	DD228247A5 (fr)
DE (1)	DE3476319D1 (fr)
DK (1)	DK167732B1 (fr)
ES (1)	ES535012A0 (fr)
FI (1)	FI82037C (fr)
GB (1)	GB2145085B (fr)
HK (1)	HK30988A (fr)
HU (1)	HU197172B (fr)
IL (1)	IL72640A (fr)
IN (1)	IN160125B (fr)
KE (1)	KE3794A (fr)
MA (1)	MA20199A1 (fr)
MX (1)	MX160550A (fr)
NO (1)	NO166752C (fr)
NZ (1)	NZ209179A (fr)
OA (1)	OA07790A (fr)
PL (1)	PL142320B1 (fr)
PT (1)	PT79062B (fr)
RO (2)	RO89127A (fr)
SG (1)	SG5088G (fr)
SU (1)	SU1565339A3 (fr)
TR (1)	TR22217A (fr)
YU (1)	YU45645B (fr)
ZW (1)	ZW12984A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4771057A (en) *	1986-02-03	1988-09-13	University Of Alberta	Reduced pyridyl derivatives with cardiovascular regulating properties
US4908057A (en) *	1988-08-01	1990-03-13	Monsanto Company	Substituted 2,6-substituted 1,2- or 1,6-dihydro pyridine compounds
US5070204A (en) *	1990-03-19	1991-12-03	Monsanto Company	Process for preparation of fluoromethyl-substituted pyridine dicarboxylates
US5116991A (en) *	1990-03-19	1992-05-26	Monsanto Company	Process for preparation of fluoromethyl-substituted dihydropyridine carbodithioates
US5099023A (en) *	1990-03-19	1992-03-24	Monsanto Company	Process for preparation of fluoromethyl-substituted pyridine carbodithioates
US5099024A (en) *	1990-03-19	1992-03-24	Monsanto Company	Process for preparation of fluoromethyl-substituted pyridine carbodithioates
HU209737B (en) *	1990-03-19	1994-10-28	Monsanto Co	Process for preparation of 4-alkyl-2,6 bis (fluoromethyl)-3,4-dihydro-pyridine- dicarboxylic acid-oxyesters and thioesters
US5206369A (en) *	1992-01-21	1993-04-27	Monsanto Company	Process for the dehydration of dihydroxypiperidinedicarboxylates
WO1999041237A1 (fr) *	1998-02-13	1999-08-19	G.D. Searle & Co.	Pyridines substituees utiles pour inhiber l'activite de la proteine assurant le transfert de l'ester de cholesteryle

1984
- 1984-08-09 ES ES535012A patent/ES535012A0/es active Granted
- 1984-08-10 DD DD84275353A patent/DD228247A5/de not_active IP Right Cessation
- 1984-08-10 EP EP84870118A patent/EP0135491B1/fr not_active Expired
- 1984-08-10 ZW ZW129/84A patent/ZW12984A1/xx unknown
- 1984-08-10 DE DE8484870118T patent/DE3476319D1/de not_active Expired
- 1984-08-10 HU HU843062A patent/HU197172B/hu not_active IP Right Cessation
- 1984-08-10 AT AT84870118T patent/ATE40262T1/de not_active IP Right Cessation
- 1984-08-10 NO NO843204A patent/NO166752C/no unknown
- 1984-08-10 OA OA58364A patent/OA07790A/fr unknown
- 1984-08-10 RO RO84115469A patent/RO89127A/fr unknown
- 1984-08-10 BG BG066569A patent/BG42832A3/xx unknown
- 1984-08-10 YU YU140084A patent/YU45645B/sh unknown
- 1984-08-10 NZ NZ209179A patent/NZ209179A/xx unknown
- 1984-08-10 AU AU31810/84A patent/AU566077B2/en not_active Ceased
- 1984-08-10 KR KR1019840004808D patent/KR890000481B1/ko not_active Expired
- 1984-08-10 SU SU843783502A patent/SU1565339A3/ru active
- 1984-08-10 CS CS846101A patent/CS261875B2/cs unknown
- 1984-08-10 DK DK385784A patent/DK167732B1/da not_active IP Right Cessation
- 1984-08-10 KR KR8404808A patent/KR870001233B1/ko not_active Expired
- 1984-08-10 PL PL1984249141A patent/PL142320B1/pl unknown
- 1984-08-10 PT PT79062A patent/PT79062B/pt not_active IP Right Cessation
- 1984-08-10 RO RO122930A patent/RO93219B/ro unknown
- 1984-08-10 MX MX5969A patent/MX160550A/es unknown
- 1984-08-10 TR TR22217A patent/TR22217A/xx unknown
- 1984-08-10 GB GB08420323A patent/GB2145085B/en not_active Expired
- 1984-08-10 IN IN597/MAS/84A patent/IN160125B/en unknown
- 1984-08-10 MA MA20423A patent/MA20199A1/fr unknown
- 1984-08-10 BR BR8404010A patent/BR8404010A/pt unknown
- 1984-08-10 CA CA460730A patent/CA1269383C/fr not_active Expired
- 1984-08-10 IL IL72640A patent/IL72640A/xx not_active IP Right Cessation
- 1984-08-10 FI FI843168A patent/FI82037C/fi not_active IP Right Cessation
1988
- 1988-01-14 SG SG50/88A patent/SG5088G/en unknown
- 1988-01-25 KE KE3794A patent/KE3794A/xx unknown
- 1988-04-28 HK HK309/88A patent/HK30988A/xx not_active IP Right Cessation
- 1988-09-02 CY CY1425A patent/CY1425A/en unknown

Also Published As

Publication number	Publication date
SG5088G (en)	1988-06-17
ZW12984A1 (en)	1984-10-17
TR22217A (tr)	1986-10-06
RO89127A (fr)	1986-04-30
NZ209179A (en)	1988-06-30
DK167732B1 (da)	1993-12-13
AU566077B2 (en)	1987-10-08
ES8506276A1 (es)	1985-07-01
RO93219A (fr)	1987-12-31
CY1425A (en)	1988-09-02
NO843204L (no)	1985-02-12
KR850001665A (ko)	1985-04-01
CS610184A2 (en)	1988-07-15
MA20199A1 (fr)	1985-04-01
KR890000481B1 (ko)	1989-03-18
DK385784D0 (da)	1984-08-10
HK30988A (en)	1988-05-06
FI843168A0 (fi)	1984-08-10
YU45645B (sh)	1992-07-20
ATE40262T1 (de)	1989-02-15
CA1269383A (fr)	1990-05-22
NO166752B (no)	1991-05-27
GB8420323D0 (en)	1984-09-12
PT79062A (en)	1984-09-01
FI82037C (fi)	1991-01-10
YU140084A (fr)	1987-10-31
GB2145085B (en)	1987-08-26
AU3181084A (en)	1985-02-14
OA07790A (fr)	1986-11-20
BG42832A3 (bg)	1988-02-15
BR8404010A (pt)	1985-07-16
IN160125B (fr)	1987-06-27
FI82037B (fi)	1990-09-28
PL249141A1 (en)	1985-08-27
HUT36671A (en)	1985-10-28
IL72640A0 (en)	1984-11-30
FI843168L (fi)	1985-02-12
ES535012A0 (es)	1985-07-01
DE3476319D1 (de)	1989-03-02
SU1565339A3 (ru)	1990-05-15
EP0135491B1 (fr)	1989-01-25
CA1269383C (fr)	1990-05-22
PT79062B (en)	1986-08-12
RO93219B (ro)	1988-01-01
KR870001233B1 (en)	1987-06-26
PL142320B1 (en)	1987-10-31
NO166752C (no)	1991-09-04
DK385784A (da)	1985-02-12
MX160550A (es)	1990-03-22
HU197172B (en)	1989-03-28
CS261875B2 (en)	1989-02-10
IL72640A (en)	1990-02-09
KE3794A (en)	1988-03-11
EP0135491A1 (fr)	1985-03-27
GB2145085A (en)	1985-03-20

Legal Events

Date	Code	Title	Description
2000-04-13	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE69133039T2 (de)	2002-10-10	Zwischenprodukte für herbizide Carboxamidderivate
EP0603649B1 (fr)	1996-07-10	4-Phenylpyridones et 4-phenyl-2-alkoxypyridines substituées comme inhibiteurs de réductase de HMG-CoA
EP0002208A1 (fr)	1979-06-13	Nitro dihydro-1,4 pyridines, médicaments les contenant et leur procédé de préparation
DE69016687T2 (de)	1995-06-08	Pyridazinone mit insektizider und acarizider Wirkung und diese enthaltende Zusammensetzungen.
DE2001017B2 (de)	1977-08-11	3,4-dihydro-1,2,3-oxathiazin-4- on-2,2-dioxide, ihre herstellung und verwendung
DD222767A5 (de)	1985-05-29	Herbizide zusammensetzung
WO1981002575A1 (fr)	1981-09-17	Derives de (1 h) -pyridinone, leur preparation et les compositions pharmaceutiques les contenant
DE2845499A1 (de)	1979-05-03	Alkanoylprolin-derivate und deren homologen, ihre herstellung und verwendung
DE2657978C3 (de)	1981-02-12	Linksdrehende Enantiomere und Racemate von Trifluormethylthio(und -sulfonyl)cyproheptadinderivaten, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
DE2407115A1 (de)	1974-10-10	Neue 1,4-dihydropyridinderivate
DE3688004T2 (de)	1993-06-24	Verfahren zur herstellung herbizider 2-(4,4-disubstituierter-5-oxo-2-imidazolin-2yl)benzoesaeuren, -nicotinsaeuren und chinolin-3-carbonsaeuren, ester und salze.
DE2726796A1 (de)	1977-12-29	Neue substituierte pyridine, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung
DE2009408A1 (de)	1970-09-17	5-Pyridyl-2-imidazolone
DE3247860C2 (fr)	1993-08-05
CZ282880B6 (cs)	1997-11-12	Způsob přípravy substituovaných a nesubstituovaných 2,3-pyridinkarboxylátů
DE3852908T2 (de)	1995-07-27	4-Halogen-3-pyridincarboxamid-Verbindungen und herbizide Zusammensetzungen daraus.
DE60015844T2 (de)	2005-10-27	Pyridin- und Piperidinderivate zur Behandlung von neurodegenerativen Erkrankungen
DD207712A5 (de)	1984-03-14	Verfahren zur herstellung von diestern
DE2919800A1 (de)	1979-11-22	4-amino-2-piperidinochinazolin-derivate, verfahren zu ihrer herstellung und solche derivate enthaltende arzneimittel
DE2822465C2 (de)	1986-08-28	2-substituierte trans-5-Phenyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indolderivate und diese enthaltende Arzneimittel
DK167732B1 (da)	1993-12-13	Herbicidt middel, fremgangsmaade til bekaempelse af uoensket plantevaekst, 2,6-bis-(fluormethyl)-dihydropyridin-3,5-dicarboxylsyreestere og fremgangsmaade til fremstilling deraf
DE3306146A1 (de)	1983-09-01	Pyridin-derivate und ihre verwendung als arzneimittel
Taylor et al.	1989	1, 3-Dipolar cycloaddition of nitrile oxides with 1, 4-dihydropyridines and conformational analysis of isoxazolo [5, 4-b] pyridines
DD235867A5 (de)	1986-05-21	Verfahren zur herstellung von 1,4-dihydropyridinen
DE68909873T2 (de)	1994-02-10	1,4-Dihydropyridin-Derivate.