DK2454242T3 - PROCESS FOR THE PREPARATION OF 3-triazolyl chiral sulfoxide DERIVATIVES - Google Patents

PROCESS FOR THE PREPARATION OF 3-triazolyl chiral sulfoxide DERIVATIVES Download PDF

Info

Publication number: DK2454242T3
Authority: DK; Denmark
Prior art keywords: alkyl; hydrogen; chiral; enantiomer; cyano
Prior art date: 2009-07-16

Application number

DK10732316.4T

Other languages

Danish (da)

English (en)

Inventor

Stefan Antons

Norbert Lui

Wahed Ahmed Moradi

Original Assignee

Bayer Ip Gmbh

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.)

2009-07-16

Filing date

2010-07-14

Publication date

2015-02-02

2010-07-14 Application filed by Bayer Ip Gmbh filed Critical Bayer Ip Gmbh

2015-02-02 Application granted granted Critical

2015-02-02 Publication of DK2454242T3 publication Critical patent/DK2454242T3/en

Links

-1 3-triazolyl Chemical group 0.000 title claims description 49
238000000034 method Methods 0.000 title claims description 34
238000002360 preparation method Methods 0.000 title description 5
150000003462 sulfoxides Chemical class 0.000 title 1
229910052739 hydrogen Inorganic materials 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 28
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
229910052731 fluorine Inorganic materials 0.000 claims description 17
239000011737 fluorine Substances 0.000 claims description 17
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 15
239000003446 ligand Substances 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 11
YZXYLAXJHXMUPM-UHFFFAOYSA-N 1-(triazol-1-ylsulfinyl)triazole Chemical class C1=CN=NN1S(=O)N1C=CN=N1 YZXYLAXJHXMUPM-UHFFFAOYSA-N 0.000 claims description 10
239000003054 catalyst Substances 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 10
125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 9
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 9
229910052723 transition metal Inorganic materials 0.000 claims description 9
150000003624 transition metals Chemical class 0.000 claims description 9
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
239000007800 oxidant agent Substances 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
125000005037 alkyl phenyl group Chemical group 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
238000002425 crystallisation Methods 0.000 claims description 6
230000008025 crystallization Effects 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
230000003647 oxidation Effects 0.000 description 9
238000007254 oxidation reaction Methods 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000004128 high performance liquid chromatography Methods 0.000 description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
230000003197 catalytic effect Effects 0.000 description 6
239000002262 Schiff base Substances 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
239000012071 phase Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
150000003568 thioethers Chemical class 0.000 description 4
150000003608 titanium Chemical class 0.000 description 4
239000010936 titanium Substances 0.000 description 4
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
150000004753 Schiff bases Chemical class 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229910052719 titanium Inorganic materials 0.000 description 3
150000003681 vanadium Chemical class 0.000 description 3
MFWFDRBPQDXFRC-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;vanadium Chemical compound [V].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MFWFDRBPQDXFRC-LNTINUHCSA-N 0.000 description 2
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
AXJXMJMPSIZOSF-UHFFFAOYSA-N 1-[2,4-dimethyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]-3-(trifluoromethyl)-1,2,4-triazole Chemical compound CC1=CC(C)=C(S(=O)CC(F)(F)F)C=C1N1N=C(C(F)(F)F)N=C1 AXJXMJMPSIZOSF-UHFFFAOYSA-N 0.000 description 2
YSAVZVORKRDODB-UHFFFAOYSA-N Diethyl tartrate Chemical compound CCOC(=O)C(O)C(O)C(=O)OCC YSAVZVORKRDODB-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
230000005526 G1 to G0 transition Effects 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000000758 substrate Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
FSJSYDFBTIVUFD-SUKNRPLKSA-N (z)-4-hydroxypent-3-en-2-one;oxovanadium Chemical compound [V]=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FSJSYDFBTIVUFD-SUKNRPLKSA-N 0.000 description 1
BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
COLOHWPRNRVWPI-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound [CH2]C(F)(F)F COLOHWPRNRVWPI-UHFFFAOYSA-N 0.000 description 1
SEQRDAAUNCRFIT-UHFFFAOYSA-N 1,1-dichlorobutane Chemical compound CCCC(Cl)Cl SEQRDAAUNCRFIT-UHFFFAOYSA-N 0.000 description 1
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 description 1
125000004515 1,2,4-thiadiazol-3-yl group Chemical group S1N=C(N=C1)* 0.000 description 1
125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 description 1
125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 1
125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 1
125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
FDMINIQYGOXHLX-UHFFFAOYSA-N 1-[2,4-dimethyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]-3-(trifluoromethyl)-1,2,4-triazole Chemical compound C1=C(SCC(F)(F)F)C(C)=CC(C)=C1N1N=C(C(F)(F)F)N=C1 FDMINIQYGOXHLX-UHFFFAOYSA-N 0.000 description 1
DLWPBFMFKDHEMF-UHFFFAOYSA-N 1-[5-(2,2-difluoroethylsulfanyl)-2,4-dimethylphenyl]-3-(difluoromethyl)-1,2,4-triazole Chemical compound C1=C(SCC(F)F)C(C)=CC(C)=C1N1N=C(C(F)F)N=C1 DLWPBFMFKDHEMF-UHFFFAOYSA-N 0.000 description 1
KOWLDGMSEGPXEO-UHFFFAOYSA-N 1-[5-(2,2-difluoroethylsulfinyl)-2,4-dimethylphenyl]-3-(difluoromethyl)-1,2,4-triazole Chemical compound CC1=CC(C)=C(S(=O)CC(F)F)C=C1N1N=C(C(F)F)N=C1 KOWLDGMSEGPXEO-UHFFFAOYSA-N 0.000 description 1
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 1
VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
CNHGNRUCVALXCV-UHFFFAOYSA-N 3-(difluoromethyl)-1-[2,4-dimethyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]-1,2,4-triazole Chemical compound C1=C(SCC(F)(F)F)C(C)=CC(C)=C1N1N=C(C(F)F)N=C1 CNHGNRUCVALXCV-UHFFFAOYSA-N 0.000 description 1
GHYSBHLFSLFTFI-UHFFFAOYSA-N 3-(difluoromethyl)-1-[2,4-dimethyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]-1,2,4-triazole Chemical compound CC1=CC(C)=C(S(=O)CC(F)(F)F)C=C1N1N=C(C(F)F)N=C1 GHYSBHLFSLFTFI-UHFFFAOYSA-N 0.000 description 1
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 1
108010081348 HRT1 protein Hairy Proteins 0.000 description 1
102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 1
UAWABSHMGXMCRK-UHFFFAOYSA-L Kagan reagent Substances I[Sm]I UAWABSHMGXMCRK-UHFFFAOYSA-L 0.000 description 1
102000008109 Mixed Function Oxygenases Human genes 0.000 description 1
108010074633 Mixed Function Oxygenases Proteins 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
108700020962 Peroxidase Proteins 0.000 description 1
102000003992 Peroxidases Human genes 0.000 description 1
ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical group CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 1
238000006202 Sharpless epoxidation reaction Methods 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
125000005595 acetylacetonate group Chemical group 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000011914 asymmetric synthesis Methods 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
230000036983 biotransformation Effects 0.000 description 1
KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000002188 cycloheptatrienyl group Chemical group C1(=CC=CC=CC1)* 0.000 description 1
125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000003821 enantio-separation Methods 0.000 description 1
ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000005826 halohydrocarbons Chemical class 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
150000002505 iron Chemical class 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
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
150000002696 manganese Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
VHILIAIEEYLJNA-UHFFFAOYSA-N methyl p-tolyl sulfide Chemical compound CSC1=CC=C(C)C=C1 VHILIAIEEYLJNA-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
150000002751 molybdenum Chemical class 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
QULYNCCPRWKEMF-UHFFFAOYSA-N parachlorobenzotrifluoride Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1 QULYNCCPRWKEMF-UHFFFAOYSA-N 0.000 description 1
BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000003579 shift reagent Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000001174 sulfone group Chemical group 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
150000003623 transition metal compounds Chemical class 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
239000002699 waste material Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
150000003754 zirconium Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Plural Heterocyclic Compounds (AREA)

DK10732316.4T 2009-07-16 2010-07-14 PROCESS FOR THE PREPARATION OF 3-triazolyl chiral sulfoxide DERIVATIVES DK2454242T3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE102009027771		2009-07-16
PCT/EP2010/004288 WO2011006646A1 (de)	2009-07-16	2010-07-14	Verfahren zur herstellung von chiralen 3-triazolyl-sulfoxid-derivaten

Publications (1)

Publication Number	Publication Date
DK2454242T3 true DK2454242T3 (en)	2015-02-02

Family

ID=42710633

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK10732316.4T DK2454242T3 (en)	2009-07-16	2010-07-14	PROCESS FOR THE PREPARATION OF 3-triazolyl chiral sulfoxide DERIVATIVES

Country Status (14)

Country	Link
US (3)	US8314133B2 (2)
EP (1)	EP2454242B1 (2)
JP (1)	JP5676602B2 (2)
KR (1)	KR20120037993A (2)
CN (1)	CN102471290B (2)
BR (1)	BR112012001078A8 (2)
DK (1)	DK2454242T3 (2)
ES (1)	ES2525535T3 (2)
IL (1)	IL217136A0 (2)
IN (1)	IN2012DN00422A (2)
MX (1)	MX2012000583A (2)
RU (1)	RU2012105122A (2)
TW (1)	TWI471314B (2)
WO (1)	WO2011006646A1 (2)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2525535T3 (es)	2009-07-16	2014-12-26	Bayer Intellectual Property Gmbh	Procedimiento para la preparación de derivados de 3-triazolil-sulfóxido quirales
EP2274982A1 (de) *	2009-07-16	2011-01-19	Bayer CropScience AG	Verwendung von Phenyltriazolen zur Bekämpfung von Insekten und Spinnmilben durch Angiessen, Tröpfchen- oder Tauchapplikation oder durch Behandlung von Saatgut
ES2494465T3 (es) *	2009-07-23	2014-09-15	Bayer Cropscience Ag	Procedimiento para la preparación de alcoxienonas y enaminocetonas
US8242313B2 (en)	2009-07-23	2012-08-14	Bayer Cropscience Ag	Alkoxy enones and enamino ketones and a process for preparation thereof
BR112012003870B1 (pt) *	2009-08-20	2018-11-21	Bayer Intellectual Property Gmbh	derivados de sulfeto substituídos com 3-triazolilfenila, seu uso, seu processo de preparação e seus intermediários, composições agroquímicas, seu processo de preparação, e processo para combate de parasitas animais
MX2012001969A (es) *	2009-08-20	2012-03-29	Bayer Cropscience Ag	Derivados de 3-[1-(3-haloalquil)-triazolil]-fenil-sulfuro como acaricidas e insecticidas.
BR112012030399A2 (pt) *	2010-06-01	2020-10-20	Kumiai Chemical Industry Co., Ltd.	composto de triazol com atividades pesticidas
EP2606726A1 (de)	2011-12-21	2013-06-26	Bayer CropScience AG	N-Arylamidine-substituierte trifluoroethylsulfid-Derivate als Akarizide und Insektizide
CN104619683B (zh)	2012-09-27	2017-05-10	拜耳农作物科学股份公司	用于制备任选地取代的苯基和吡啶基吡咯烷类的方法
AR093909A1 (es)	2012-12-12	2015-06-24	Bayer Cropscience Ag	Uso de ingredientes activos para controlar nematodos en cultivos resistentes a nematodos
WO2015036380A1 (de)	2013-09-13	2015-03-19	Bayer Cropscience Ag	Verfahren zur reduktion von arylsulfoxiden zu arylthioethern
WO2015135984A1 (de)	2014-03-13	2015-09-17	Bayer Cropscience Ag	Verfahren zur herstellung von chiralen 3-(5-aminotriazolyl)-sulfoxid-derivaten
CN111246742B (zh) *	2017-10-18	2022-09-23	拜耳公司	具有杀虫/杀螨特性的活性化合物结合物
WO2021084074A1 (en)	2019-10-30	2021-05-06	Solvay Sa	Compositions and films comprising a polymer and tis2 particles, and their preparation and uses
MX2022012405A (es)	2020-04-30	2023-01-11	Kumiai Chemical Industry Co	Metodo para producir derivados de monosulfoxido.
BR112023017032A2 (pt)	2021-03-26	2023-11-14	Bayer Ag	Processo para preparar derivados de sulfóxido de (2z)-2-(fenilimino)-1,3-tiazolidin-4-ona enantiomericamente enriquecidos

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU3536699A (en) *	1998-04-27	1999-11-16	Ihara Chemical Industry Co. Ltd.	3-arylphenyl sulfide derivatives and insecticides and miticides
FR2852956B1 (fr) *	2003-03-28	2006-08-04	Negma Gild	Procede de preparation enantioselective de derives de sulfoxydes
FR2863611B1 (fr) *	2003-12-15	2006-03-24	Sidem Pharma Sa	Procede de preparation enantioselective de derives de sulfoxydes
EP1608649A2 (fr)	2003-03-28	2005-12-28	Sidem Pharma SA	Procede de preparation enantioselective de derives de sulfoxydes.
EP1516869A1 (en) *	2003-09-19	2005-03-23	Cephalon France	Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation
FR2876101B1 (fr) *	2004-10-05	2007-03-02	Sidem Pharma Sa Sa	Procede de preparation enantioselective de derives de sulfoxydes
ATE443051T1 (de) *	2004-10-11	2009-10-15	Ranbaxy Lab Ltd	Verfahren zur herstellung substituierter sulfoxide
CA2581725C (en) *	2004-10-20	2013-01-08	Kumiai Chemical Industry Co., Ltd.	3-triazolylphenyl sulfide derivative, and insecticide, miticide and nematicide containing it as an active ingredient
CN101012141B (zh) *	2007-02-02	2012-05-23	沈阳药科大学	手性亚砜类化合物的制备方法
CN103664811B (zh) *	2007-11-30	2015-09-16	庵原化学工业株式会社	(1h-1,2,4-三唑-1-基)芳基化合物及其制备方法
CN101323582A (zh) *	2008-07-30	2008-12-17	大连理工大学	一类手性西佛碱配体及其在硫醚不对称氧化反应中的应用
CN101429192A (zh) *	2008-08-22	2009-05-13	扬子江药业集团有限公司	生产手性亚砜衍生物的新方法
EP2274982A1 (de)	2009-07-16	2011-01-19	Bayer CropScience AG	Verwendung von Phenyltriazolen zur Bekämpfung von Insekten und Spinnmilben durch Angiessen, Tröpfchen- oder Tauchapplikation oder durch Behandlung von Saatgut
ES2525535T3 (es)	2009-07-16	2014-12-26	Bayer Intellectual Property Gmbh	Procedimiento para la preparación de derivados de 3-triazolil-sulfóxido quirales
MX2012001969A (es) *	2009-08-20	2012-03-29	Bayer Cropscience Ag	Derivados de 3-[1-(3-haloalquil)-triazolil]-fenil-sulfuro como acaricidas e insecticidas.
BR112012003870B1 (pt) *	2009-08-20	2018-11-21	Bayer Intellectual Property Gmbh	derivados de sulfeto substituídos com 3-triazolilfenila, seu uso, seu processo de preparação e seus intermediários, composições agroquímicas, seu processo de preparação, e processo para combate de parasitas animais

2010
- 2010-07-14 ES ES10732316.4T patent/ES2525535T3/es active Active
- 2010-07-14 WO PCT/EP2010/004288 patent/WO2011006646A1/de not_active Ceased
- 2010-07-14 MX MX2012000583A patent/MX2012000583A/es active IP Right Grant
- 2010-07-14 JP JP2012519925A patent/JP5676602B2/ja not_active Expired - Fee Related
- 2010-07-14 RU RU2012105122/04A patent/RU2012105122A/ru not_active Application Discontinuation
- 2010-07-14 IN IN422DEN2012 patent/IN2012DN00422A/en unknown
- 2010-07-14 DK DK10732316.4T patent/DK2454242T3/en active
- 2010-07-14 EP EP10732316.4A patent/EP2454242B1/de not_active Not-in-force
- 2010-07-14 BR BR112012001078A patent/BR112012001078A8/pt active Search and Examination
- 2010-07-14 CN CN201080031476.1A patent/CN102471290B/zh not_active Expired - Fee Related
- 2010-07-14 KR KR1020127003961A patent/KR20120037993A/ko not_active Withdrawn
- 2010-07-15 TW TW99123228A patent/TWI471314B/zh not_active IP Right Cessation
- 2010-07-16 US US12/837,646 patent/US8314133B2/en not_active Expired - Fee Related
2011
- 2011-12-22 IL IL217136A patent/IL217136A0/en unknown
2012
- 2012-10-15 US US13/652,039 patent/US8765970B2/en not_active Expired - Fee Related
2014
- 2014-05-15 US US14/278,132 patent/US20140256953A1/en not_active Abandoned

Also Published As

Publication number	Publication date
EP2454242B1 (de)	2014-10-15
JP2012532906A (ja)	2012-12-20
BR112012001078A2 (pt)	2015-09-01
US20140256953A1 (en)	2014-09-11
MX2012000583A (es)	2012-02-13
US20110015405A1 (en)	2011-01-20
US20130172573A1 (en)	2013-07-04
WO2011006646A1 (de)	2011-01-20
RU2012105122A (ru)	2013-08-27
JP5676602B2 (ja)	2015-02-25
BR112012001078A8 (pt)	2016-05-03
IN2012DN00422A (2)	2015-05-15
US8765970B2 (en)	2014-07-01
IL217136A0 (en)	2012-02-29
TW201116517A (en)	2011-05-16
ES2525535T3 (es)	2014-12-26
KR20120037993A (ko)	2012-04-20
CN102471290A (zh)	2012-05-23
CN102471290B (zh)	2016-02-03
US8314133B2 (en)	2012-11-20
EP2454242A1 (de)	2012-05-23
TWI471314B (zh)	2015-02-01

Publication	Publication Date	Title
US8765970B2 (en)	2014-07-01	Process for preparing chiral 3-triazolyl sulphoxide derivatives
Yu et al.	2012	Palladium-catalyzed desulfitative arylation of azoles with arylsulfonyl hydrazides
Patil et al.	2012	Copper (0)-catalyzed aerobic oxidative synthesis of imines from amines under solvent-free conditions
Mitchell et al.	2005	A versatile organocatalyst for the asymmetric conjugate addition of nitroalkanes to enones
Shirakawa et al.	2012	The direct catalytic asymmetric aldol reaction of α-substituted nitroacetates with aqueous formaldehyde under base-free neutral phase-transfer conditions
Kitanosono et al.	2012	Chiral-Sc catalyzed asymmetric Michael addition/protonation of thiols with enones in water
JP2015096515A (ja)	2015-05-21	ルフィナマイドの製造方法
JP2008504260A5 (2)	2008-08-07
CN104220419B (zh)	2017-03-29	含cf3o的烯胺酮和它们用于制备含cf3o的吡唑类的用途
Wei et al.	2009	KI-catalyzed aminobromination of olefins with TsNH 2–NBS combination
US11691943B2 (en)	2023-07-04	Preparation method of 4-(heptafluoro-2-propyl)-2-trifluoromethylaniline and application thereof
Debiais et al.	2020	Bio-inspired NHC-organocatalyzed Stetter reaction in aqueous conditions
TW202304870A (zh)	2023-02-01	製備鏡像異構富集之（２ｚ）－２－（苯亞胺基）－１，３－四氫噻唑－４－酮亞碸衍生物的方法
EP2858966A1 (fr)	2015-04-15	Procede de creation de liaisons carbone-carbone a partir de composes carbonyles
Bera et al.	2015	Bimetallic titanium complex catalyzed enantioselective oxidation of thioethers using aqueous H 2 O 2 as a terminal oxidant
CN106866558B (zh)	2019-07-30	酰基三氮唑类化合物及其制备方法和应用
JP2010215513A (ja)	2010-09-30	α付加型アリル化反応による選択的ホモアリルアルコール誘導体の製造法
WO2015135984A1 (de)	2015-09-17	Verfahren zur herstellung von chiralen 3-(5-aminotriazolyl)-sulfoxid-derivaten
WO2023054429A1 (ja)	2023-04-06	アルキルフランカルボン酸エステルの製造方法
Hara et al.	2008	Fluorous Thlazolium Salts for the Intramolecular Stetter Reaction
CN103588721B (zh)	2015-07-29	2-(2-苯并-1,3-二唑)-2,2-二氟-1-芳基乙醇类化合物及其制备方法
WO2004069807A1 (fr)	2004-08-19	Procede de preparation d'un reactif de type acylimidazolium
JP2007191402A (ja)	2007-08-02	２−イミダゾリジノン化合物の製法