NO315465B1 - Fremgangsmåte for fremstilling av arylamider av heteroaromatiske karboksylsyrer - Google Patents

Fremgangsmåte for fremstilling av arylamider av heteroaromatiske karboksylsyrer Download PDF

Info

Publication number: NO315465B1
Authority: NO; Norway
Prior art keywords: nitrogen; ring; optionally substituted; formula; alkyl
Prior art date: 1996-03-21

Application number

NO19971315A

Other languages

English (en)

Norwegian (no)

Other versions

NO971315L (no

NO971315D0 (no

Inventor

Jean-Paul Roduit

Georges Kalbermatten

Original Assignee

Lonza Ag

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.)

1996-03-21

Filing date

1997-03-20

Publication date

2003-09-08

1997-03-20 Application filed by Lonza Ag filed Critical Lonza Ag

1997-03-20 Publication of NO971315D0 publication Critical patent/NO971315D0/no

1997-09-22 Publication of NO971315L publication Critical patent/NO971315L/no

2003-09-08 Publication of NO315465B1 publication Critical patent/NO315465B1/no

Links

238000000034 method Methods 0.000 title claims abstract description 33
-1 heteroaromatic carboxylic acids Chemical class 0.000 title claims abstract description 23
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 37
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 23
VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims abstract description 14
229910052763 palladium Inorganic materials 0.000 claims abstract description 10
125000003118 aryl group Chemical group 0.000 claims abstract description 9
150000002366 halogen compounds Chemical class 0.000 claims abstract description 9
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 8
229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 8
229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
229910052794 bromium Inorganic materials 0.000 claims abstract description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
229910052723 transition metal Inorganic materials 0.000 claims abstract description 5
150000003624 transition metals Chemical class 0.000 claims abstract description 5
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
150000001412 amines Chemical class 0.000 claims abstract description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 62
150000001408 amides Chemical class 0.000 claims description 26
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000001624 naphthyl group Chemical group 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
125000002541 furyl group Chemical group 0.000 claims description 7
125000001041 indolyl group Chemical group 0.000 claims description 7
125000003226 pyrazolyl group Chemical group 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
125000000168 pyrrolyl group Chemical group 0.000 claims description 7
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
125000001544 thienyl group Chemical group 0.000 claims description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 3
KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
125000003373 pyrazinyl group Chemical group 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 20
125000000217 alkyl group Chemical group 0.000 abstract description 11
238000006243 chemical reaction Methods 0.000 abstract description 6
238000004519 manufacturing process Methods 0.000 abstract description 4
125000001072 heteroaryl group Chemical group 0.000 abstract description 2
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 abstract 1
125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
101150065749 Churc1 gene Proteins 0.000 abstract 1
102100038239 Protein Churchill Human genes 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
229910052740 iodine Inorganic materials 0.000 abstract 1
229920006395 saturated elastomer Polymers 0.000 abstract 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 19
239000000203 mixture Substances 0.000 description 19
239000000047 product Substances 0.000 description 19
239000008096 xylene Substances 0.000 description 19
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
239000012071 phase Substances 0.000 description 13
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
239000006227 byproduct Substances 0.000 description 11
150000003335 secondary amines Chemical class 0.000 description 11
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
CWKFPEBMTGKLKX-UHFFFAOYSA-N picolinafen Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 CWKFPEBMTGKLKX-UHFFFAOYSA-N 0.000 description 8
UXNQGJXYCPLETH-UHFFFAOYSA-N C1(=CC=CC=C1)P(C=1[C-](C=CC1)C(C)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.[CH-]1C=CC=C1.[Fe+2] Chemical compound C1(=CC=CC=C1)P(C=1[C-](C=CC1)C(C)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.[CH-]1C=CC=C1.[Fe+2] UXNQGJXYCPLETH-UHFFFAOYSA-N 0.000 description 7
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 7
229910000029 sodium carbonate Inorganic materials 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 5
239000007787 solid Substances 0.000 description 5
KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000002904 solvent Substances 0.000 description 4
LFVNBAYLMRRFQM-UHFFFAOYSA-N 2-chloro-6-[3-(trifluoromethyl)phenoxy]pyridine Chemical compound FC(F)(F)C1=CC=CC(OC=2N=C(Cl)C=CC=2)=C1 LFVNBAYLMRRFQM-UHFFFAOYSA-N 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
OHWWNYSXSGMTSB-UHFFFAOYSA-N cyclopenta-1,3-diene;ditert-butyl-[1-(2-diphenylphosphanylcyclopenta-2,4-dien-1-yl)ethyl]phosphane;iron(2+) Chemical compound [Fe+2].C=1C=C[CH-]C=1.CC(C)(C)P(C(C)(C)C)C(C)[C-]1C=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 OHWWNYSXSGMTSB-UHFFFAOYSA-N 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
229940031826 phenolate Drugs 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
102220007331 rs111033633 Human genes 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000007858 starting material Substances 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
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
WVSBQYMJNMJHIM-UHFFFAOYSA-N (benzene)chromium tricarbonyl Chemical group [Cr].[O+]#[C-].[O+]#[C-].[O+]#[C-].C1=CC=CC=C1 WVSBQYMJNMJHIM-UHFFFAOYSA-N 0.000 description 1
QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
BINQYVWLAWZYPX-UHFFFAOYSA-N 1,3,5-triazine-2-carboxylic acid Chemical class OC(=O)C1=NC=NC=N1 BINQYVWLAWZYPX-UHFFFAOYSA-N 0.000 description 1
MAKFMOSBBNKPMS-UHFFFAOYSA-N 2,3-dichloropyridine Chemical compound ClC1=CC=CN=C1Cl MAKFMOSBBNKPMS-UHFFFAOYSA-N 0.000 description 1
CEPCPXLLFXPZGW-UHFFFAOYSA-N 2,4-difluoroaniline Chemical compound NC1=CC=C(F)C=C1F CEPCPXLLFXPZGW-UHFFFAOYSA-N 0.000 description 1
FILKGCRCWDMBKA-UHFFFAOYSA-N 2,6-dichloropyridine Chemical compound ClC1=CC=CC(Cl)=N1 FILKGCRCWDMBKA-UHFFFAOYSA-N 0.000 description 1
MFDBYHAXXAGPNF-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenoxy]pyridine Chemical compound FC(F)(F)C1=CC=CC(OC=2N=CC=CC=2)=C1 MFDBYHAXXAGPNF-UHFFFAOYSA-N 0.000 description 1
ZZXWXGVXVLZNFK-UHFFFAOYSA-N 2-chloro-6-[3-(trifluoromethyl)phenoxy]pyrazine Chemical compound FC(F)(F)C1=CC=CC(OC=2N=C(Cl)C=NC=2)=C1 ZZXWXGVXVLZNFK-UHFFFAOYSA-N 0.000 description 1
UGEJOEBBMPOJMT-UHFFFAOYSA-N 3-(trifluoromethyl)phenol Chemical compound OC1=CC=CC(C(F)(F)F)=C1 UGEJOEBBMPOJMT-UHFFFAOYSA-N 0.000 description 1
JHFQIWDOKUTRBA-UHFFFAOYSA-N 3-chloro-2-[3-(trifluoromethyl)phenoxy]pyridine Chemical compound FC(F)(F)C1=CC=CC(OC=2C(=CC=CN=2)Cl)=C1 JHFQIWDOKUTRBA-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XRGZZAZQHRUQLU-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C(=NC(=CC1)OC1=CC(=CC=C1)C(F)(F)F)C(=O)N Chemical compound FC1=CC=C(C=C1)C=1C(=NC(=CC1)OC1=CC(=CC=C1)C(F)(F)F)C(=O)N XRGZZAZQHRUQLU-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
238000009876 asymmetric hydrogenation reaction Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
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
YLQBEKUKMJWXMC-UHFFFAOYSA-N cyclopenta-1,3-diene cyclopenta-2,4-dien-1-ylphosphane iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.P[c-]1cccc1 YLQBEKUKMJWXMC-UHFFFAOYSA-N 0.000 description 1
125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
GUZQPNDMHDZWCJ-UHFFFAOYSA-N ethyl-di(propan-2-yl)phosphane Chemical compound CCP(C(C)C)C(C)C GUZQPNDMHDZWCJ-UHFFFAOYSA-N 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
DWYVYJAYIWUNHX-UHFFFAOYSA-N n-(4-fluorophenyl)-6-[3-(trifluoromethyl)phenoxy]pyrazine-2-carboxamide Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CN=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 DWYVYJAYIWUNHX-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical group 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
102220029346 rs34541442 Human genes 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
BFMKBYZEJOQYIM-UCGGBYDDSA-N tert-butyl (2s,4s)-4-diphenylphosphanyl-2-(diphenylphosphanylmethyl)pyrrolidine-1-carboxylate Chemical compound C([C@@H]1C[C@@H](CN1C(=O)OC(C)(C)C)P(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 BFMKBYZEJOQYIM-UCGGBYDDSA-N 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
235000019798 tripotassium phosphate Nutrition 0.000 description 1
230000007306 turnover Effects 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
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- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/80—Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
- B01J2523/82—Metals of the platinum group
- B01J2523/824—Palladium
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/80—Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
- B01J2523/84—Metals of the iron group
- B01J2523/842—Iron
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/842—Iron

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Inorganic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

NO19971315A 1996-03-21 1997-03-20 Fremgangsmåte for fremstilling av arylamider av heteroaromatiske karboksylsyrer NO315465B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH73596		1996-03-21

Publications (3)

Publication Number	Publication Date
NO971315D0 NO971315D0 (no)	1997-03-20
NO971315L NO971315L (no)	1997-09-22
NO315465B1 true NO315465B1 (no)	2003-09-08

Family

ID=4193980

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19971315A NO315465B1 (no)	1996-03-21	1997-03-20	Fremgangsmåte for fremstilling av arylamider av heteroaromatiske karboksylsyrer

Country Status (17)

Country	Link
US (2)	US5922870A (fr)
EP (1)	EP0798296B1 (fr)
JP (1)	JP4138905B2 (fr)
KR (1)	KR100508740B1 (fr)
CN (1)	CN1071320C (fr)
AT (1)	ATE256113T1 (fr)
CA (2)	CA2199786C (fr)
CZ (1)	CZ289783B6 (fr)
DE (1)	DE59711086D1 (fr)
DK (1)	DK0798296T3 (fr)
ES (1)	ES2212005T3 (fr)
HU (1)	HU220171B (fr)
NO (1)	NO315465B1 (fr)
PL (1)	PL191593B1 (fr)
PT (1)	PT798296E (fr)
SK (1)	SK284024B6 (fr)
TW (1)	TW472044B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2212005T3 (es) *	1996-03-21	2004-07-16	Lonza Ag	Procedimiento para preparar arilamidas de acidos carboxilicos heteroaromaticos.
US7912205B2 (en) *	2004-12-17	2011-03-22	Aspect Software, Inc.	Contact center business modeler

Family Cites Families (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4128554A (en) *	1974-05-10	1978-12-05	University Of Delaware	Process for the preparation of carboxylic acid amides from organic halides
NZ188244A (en) *	1977-09-13	1981-04-24	Ici Australia Ltd	2-substituted pyrimidines compositions growth regulating processes
US4254125A (en) *	1980-04-07	1981-03-03	The Dow Chemical Company	2-Chloro-3-phenoxypyrazines and 2-chloro-6-phenoxypyrazines possessing antiviral activity
IL64220A (en) *	1980-11-21	1985-06-30	May & Baker Ltd	Nicotinamide derivatives,their preparation and their use as herbicides
US5159113A (en) *	1984-12-19	1992-10-27	The B. F. Goodrich Company	Process for the palladium-catalyzed amidation of vinyl chloride
CH664754A5 (en) *	1985-06-25	1988-03-31	Lonza Ag	5,6-di:chloro-nicotinic acid prodn. - by reacting 6-hydroxy-nicotinic acid with acid chloride, reacting prod. with chlorine, then with acid chloride and hydrolysing prod
JPS62138472A (ja) *	1985-12-11	1987-06-22	Mitsui Toatsu Chem Inc	２，６−ビス（４−アミノフエノキシ）ピリジンおよびその製造方法
JPS62142161A (ja) *	1985-12-16	1987-06-25	Mitsui Toatsu Chem Inc	２，６−ビス（３−カルボキシフエノキシ）ピリジンおよびその製造方法
JPH0819009B2 (ja) *	1987-03-12	1996-02-28	日本農薬株式会社	カルボン酸アミド類の製造法
IL91083A (en) *	1988-07-25	1993-04-04	Ciba Geigy	Cyclohexanedione derivatives, their preparation and their use as herbicides
CA2245055C (fr) *	1989-02-28	2003-03-25	F. Hoffmann-La Roche Ag	Amidation des pyridines
DE4020055A1 (de) *	1990-01-18	1991-07-25	Bayer Ag	Verfahren zur herstellung von substituierten 2-chlor-pyridinen
GB9005965D0 (en) *	1990-03-16	1990-05-09	Shell Int Research	Herbicidal carboxamide derivatives
EP0461401A1 (fr) *	1990-06-15	1991-12-18	American Cyanamid Company	Procédé pour la préparation des esters dialcoyliques 2,3-dicarboxy-pyridine et leurs dérivés à partir des esters dichloromaléiques
GB9025828D0 (en) *	1990-11-28	1991-01-09	Shell Int Research	Herbicidal carboxamide derivatives
DE4207604A1 (de) *	1991-03-13	1992-09-17	Ciba Geigy Ag	Schaedlingsbekaempfungsmittel
US5166352A (en) *	1991-09-12	1992-11-24	Dowelanco	Pyridinecarboxylic acid chlorides from (trichloromethyl)pyridines
US5288866A (en) *	1991-12-20	1994-02-22	American Cyanamid Company	5,6-disubstituted-3-pyridylmethyl ammonium halide compounds useful for the preparation of 5- (substituted methyl)-2,3-pyridinedicarboxylic acids
EP0564406B1 (fr) *	1992-04-02	1999-05-06	Novartis AG	Ferrocenyldiphosphine comme ligandes de catalyseurs homogènes
EP0612758B1 (fr) *	1993-02-26	2003-04-09	Syngenta Participations AG	Ferrocenyl diphosphines comme ligands pour des catalyseurs homogènes
WO1994027974A1 (fr) *	1993-05-27	1994-12-08	Shell Internationale Research Maatschappij B.V.	Herbicides
CA2539969C (fr) *	1993-06-01	2009-07-07	Lonza Ltd.	Methode de preparation d'acides carboxyliques a partir de composes heterocycliques aromatiques renfermant de l'azote
EP0646590B1 (fr) *	1993-10-01	1999-08-25	Novartis AG	Ferrocényldiphosphines substituées par un groupe fluoroalkyle comme ligands pour des catalyseurs homogènes
DE4410480A1 (de) *	1994-03-25	1995-09-28	Hoechst Ag	Sulfonamidocarbonylpyridin-2-carbonsäureesteramide sowie ihre Pyridin-N-oxide, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
US5464106A (en) *	1994-07-06	1995-11-07	Plastipak Packaging, Inc.	Multi-layer containers
ES2212005T3 (es) *	1996-03-21	2004-07-16	Lonza Ag	Procedimiento para preparar arilamidas de acidos carboxilicos heteroaromaticos.
DE59701125D1 (de) *	1996-05-09	2000-03-23	Lonza Ag	Verfahren zur Herstellung von Arylamiden heteroaromatischer Carbonsäuren
US5900484A (en) *	1996-09-18	1999-05-04	Lonza Ag	Process for the preparation of arylamides of heteroaromatic carboxylic acids

1997
- 1997-03-10 ES ES97103981T patent/ES2212005T3/es not_active Expired - Lifetime
- 1997-03-10 DK DK97103981T patent/DK0798296T3/da active
- 1997-03-10 EP EP97103981A patent/EP0798296B1/fr not_active Expired - Lifetime
- 1997-03-10 PT PT97103981T patent/PT798296E/pt unknown
- 1997-03-10 AT AT97103981T patent/ATE256113T1/de not_active IP Right Cessation
- 1997-03-10 DE DE59711086T patent/DE59711086D1/de not_active Expired - Fee Related
- 1997-03-12 CA CA002199786A patent/CA2199786C/fr not_active Expired - Fee Related
- 1997-03-12 SK SK322-97A patent/SK284024B6/sk not_active IP Right Cessation
- 1997-03-12 CA CA002504399A patent/CA2504399C/fr not_active Expired - Fee Related
- 1997-03-13 US US08/816,692 patent/US5922870A/en not_active Expired - Fee Related
- 1997-03-14 JP JP06135897A patent/JP4138905B2/ja not_active Expired - Fee Related
- 1997-03-15 TW TW086103236A patent/TW472044B/zh not_active IP Right Cessation
- 1997-03-18 KR KR1019970009205A patent/KR100508740B1/ko not_active Expired - Fee Related
- 1997-03-20 NO NO19971315A patent/NO315465B1/no not_active IP Right Cessation
- 1997-03-20 HU HU9700616A patent/HU220171B/hu not_active IP Right Cessation
- 1997-03-20 CZ CZ1997852A patent/CZ289783B6/cs not_active IP Right Cessation
- 1997-03-21 CN CN97104882A patent/CN1071320C/zh not_active Expired - Lifetime
- 1997-03-21 PL PL319086A patent/PL191593B1/pl not_active IP Right Cessation
1999
- 1999-03-30 US US09/280,975 patent/US6175011B1/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2504399C (fr)	2009-09-15
PT798296E (pt)	2004-04-30
SK284024B6 (sk)	2004-08-03
TW472044B (en)	2002-01-11
NO971315L (no)	1997-09-22
JPH107655A (ja)	1998-01-13
EP0798296A2 (fr)	1997-10-01
US6175011B1 (en)	2001-01-16
US5922870A (en)	1999-07-13
HU220171B (hu)	2001-11-28
ES2212005T3 (es)	2004-07-16
DE59711086D1 (de)	2004-01-22
EP0798296B1 (fr)	2003-12-10
HU9700616D0 (en)	1997-05-28
PL191593B1 (pl)	2006-06-30
ATE256113T1 (de)	2003-12-15
PL319086A1 (en)	1997-09-29
CA2199786C (fr)	2005-08-09
KR100508740B1 (ko)	2006-03-23
CN1169990A (zh)	1998-01-14
JP4138905B2 (ja)	2008-08-27
HUP9700616A2 (en)	1997-12-29
KR970065518A (ko)	1997-10-13
HUP9700616A3 (en)	1999-05-28
NO971315D0 (no)	1997-03-20
EP0798296A3 (fr)	1999-01-13
CA2504399A1 (fr)	1997-09-21
CN1071320C (zh)	2001-09-19
SK32297A3 (en)	1998-01-14
CZ289783B6 (cs)	2002-04-17
CZ85297A3 (en)	1997-10-15
CA2199786A1 (fr)	1997-09-21
DK0798296T3 (da)	2004-04-05

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Date	Code	Title	Description
2010-11-01	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
BR112014019487A2 (pt)	2020-10-27	processo para preparar derivados de ácidos antranílico substituídos
Kadari et al.	2020	Iodoferrocene as a partner in N-arylation of amides
US5922870A (en)	1999-07-13	Process for the preparation of arylamides of heteroaromatic carboxylic acids
US6635766B1 (en)	2003-10-21	Process for the preparation of arylamides of heteroaromatic carboxylic acids
Cropper et al.	2009	Delineating ligand effects in intramolecular aryl amidation reactions: formation of a novel spiro-heterocycle by a tandem cyclisation process
JP4103153B2 (ja)	2008-06-18	複素環式芳香族カルボン酸のアリールアミドの製造方法
US5900484A (en)	1999-05-04	Process for the preparation of arylamides of heteroaromatic carboxylic acids
US6441233B1 (en)	2002-08-27	Process for the preparation of aromatic carboxylic acid amides
TW202517655A (zh)	2025-05-01	使用［Ｃｕ（μ－ｓａｌｂｅｎ）］錯合物之Ｃ－Ｎ偶合方法
JP2007119399A (ja)	2007-05-17	Ｎ−保護−２−アミノペンタン酸誘導体の製造方法
Wagaw	1999	Development and application of palladium-catalyzed carbon-nitrogen bond forming reactions