KR101164694B1 - 피리딘 유도체의 제조 방법 - Google Patents
피리딘 유도체의 제조 방법 Download PDFInfo
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- KR101164694B1 KR101164694B1 KR1020067012653A KR20067012653A KR101164694B1 KR 101164694 B1 KR101164694 B1 KR 101164694B1 KR 1020067012653 A KR1020067012653 A KR 1020067012653A KR 20067012653 A KR20067012653 A KR 20067012653A KR 101164694 B1 KR101164694 B1 KR 101164694B1
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- South Korea
- Prior art keywords
- formula
- alkyl
- alkoxy
- aryl
- aryloxy
- Prior art date
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- 150000003222 pyridines Chemical class 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 23
- 150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 44
- 229910052801 chlorine Inorganic materials 0.000 claims description 29
- 229910052794 bromium Inorganic materials 0.000 claims description 27
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 229910052740 iodine Inorganic materials 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004122 cyclic group Chemical group 0.000 claims description 17
- 229910052799 carbon Chemical group 0.000 claims description 16
- 239000000543 intermediate Substances 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 9
- 229910021536 Zeolite Inorganic materials 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 8
- 239000010457 zeolite Substances 0.000 claims description 8
- IKHLLNMSMFVTLP-UHFFFAOYSA-N 4-(trifluoromethyl)-1h-pyridin-2-one Chemical compound OC1=CC(C(F)(F)F)=CC=N1 IKHLLNMSMFVTLP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 claims description 4
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- DHJDPIHFALRNER-OWOJBTEDSA-N (e)-4-amino-1,1,1-trifluorobut-3-en-2-one Chemical compound N\C=C\C(=O)C(F)(F)F DHJDPIHFALRNER-OWOJBTEDSA-N 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 23
- XPYGGHVSFMUHLH-UUSULHAXSA-N falecalcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(O)(C(F)(F)F)C(F)(F)F)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C XPYGGHVSFMUHLH-UUSULHAXSA-N 0.000 abstract description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- -1 6-substituted pyridine Chemical class 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 125000004093 cyano group Chemical group *C#N 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 125000004494 ethyl ester group Chemical group 0.000 description 8
- 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 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- WCWACXRUGJZEMU-UHFFFAOYSA-N 2-[hydroxy(methoxy)phosphinothioyl]acetonitrile Chemical compound COP(=S)(O)CC#N WCWACXRUGJZEMU-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical compound CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 description 5
- UVIJMESDQMPSLI-UHFFFAOYSA-N 1,1-diethoxy-2-(trifluoromethyl)pent-1-ene Chemical compound FC(F)(F)C(=C(OCC)OCC)CCC UVIJMESDQMPSLI-UHFFFAOYSA-N 0.000 description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000003905 agrochemical Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- CERDCNUMTCLHAP-UHFFFAOYSA-N 2-ethoxy-4-(trifluoromethyl)pyridine Chemical compound CCOC1=CC(C(F)(F)F)=CC=N1 CERDCNUMTCLHAP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 239000012159 carrier gas Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 150000002900 organolithium compounds Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- OWSHOFSFNSRRMF-UHFFFAOYSA-N 1-ethoxy-4,4,4-trifluorobut-1-ene Chemical compound CCOC=CCC(F)(F)F OWSHOFSFNSRRMF-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
- 238000006052 Horner reaction Methods 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- SAFQZYRQIXIKDC-UHFFFAOYSA-N cyanomethylphosphonic acid Chemical compound OP(O)(=O)CC#N SAFQZYRQIXIKDC-UHFFFAOYSA-N 0.000 description 2
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 229910000103 lithium hydride Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 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
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- GRCBQYDZUYASQL-UHFFFAOYSA-N 1,1-diethoxy-3-(trifluoromethyl)pent-1-ene Chemical compound FC(C(C=C(OCC)OCC)CC)(F)F GRCBQYDZUYASQL-UHFFFAOYSA-N 0.000 description 1
- IAPHALVOYNQNCU-UHFFFAOYSA-N 1-amino-5,5,5-trifluoropent-1-en-3-one Chemical compound NC=CC(=O)CC(F)(F)F IAPHALVOYNQNCU-UHFFFAOYSA-N 0.000 description 1
- ATRQECRSCHYSNP-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC=N1 ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- GGKAAPYKPQEJOK-UHFFFAOYSA-N 3-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical compound CCOC(=C)C(=O)C(F)(F)F GGKAAPYKPQEJOK-UHFFFAOYSA-N 0.000 description 1
- AHZDTXAEITWOEF-UHFFFAOYSA-N 5,5-diethoxy-2-methylsulfanyl-3-(trifluoromethyl)pent-2-enenitrile Chemical compound CCOC(OCC)CC(=C(SC)C#N)C(F)(F)F AHZDTXAEITWOEF-UHFFFAOYSA-N 0.000 description 1
- JNYLMODTPLSLIF-UHFFFAOYSA-N 6-(trifluoromethyl)pyridine-3-carboxylic acid Chemical group OC(=O)C1=CC=C(C(F)(F)F)N=C1 JNYLMODTPLSLIF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- 0 CC(C(C)(*)*)C=CN Chemical compound CC(C(C)(*)*)C=CN 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 238000003482 Pinner synthesis reaction Methods 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 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
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 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
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid group Chemical group C(CCCCCC)(=O)O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000006198 methoxylation reaction Methods 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000007944 thiolates Chemical group 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53161403P | 2003-12-23 | 2003-12-23 | |
| US60/531,614 | 2003-12-23 | ||
| EP03029730 | 2003-12-23 | ||
| EP03029730.3 | 2003-12-23 | ||
| PCT/EP2004/014590 WO2005063780A1 (en) | 2003-12-23 | 2004-12-22 | Process for the preparation of pyridine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20060128896A KR20060128896A (ko) | 2006-12-14 |
| KR101164694B1 true KR101164694B1 (ko) | 2012-07-11 |
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| KR1020067012653A KR101164694B1 (ko) | 2003-12-23 | 2004-12-22 | 피리딘 유도체의 제조 방법 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1732895B1 (en) * | 2004-04-08 | 2016-11-16 | Dow AgroSciences LLC | Insecticidal n-substituted sulfoximines |
| US7488828B2 (en) * | 2004-06-25 | 2009-02-10 | Dow Agrosciences Llc | Process for the preparation of 4-trifluoromethyl-2(1H)-pyridinone |
| TWI398433B (zh) * | 2006-02-10 | 2013-06-11 | Dow Agrosciences Llc | 殺蟲性之ｎ-取代（６-鹵烷基吡啶-３-基）烷基磺醯亞胺 |
| TWI381811B (zh) * | 2006-06-23 | 2013-01-11 | Dow Agrosciences Llc | 用以防治可抵抗一般殺蟲劑之昆蟲的方法 |
| TWI387585B (zh) * | 2006-09-01 | 2013-03-01 | Dow Agrosciences Llc | 殺蟲性之ｎ-取代（雜芳基）烷基烴基硫亞胺 |
| KR101393850B1 (ko) * | 2006-09-01 | 2014-05-12 | 다우 아그로사이언시즈 엘엘씨 | 살충성 ｎ-치환된 (2-치환된-1,3-티아졸)알킬 술폭시민 |
| TWI395736B (zh) * | 2006-11-08 | 2013-05-11 | Dow Agrosciences Llc | 作為殺蟲劑之雜芳基（取代的）烷基ｎ-取代的磺醯亞胺（二） |
| US7709648B2 (en) * | 2007-02-09 | 2010-05-04 | Dow Agrosciences Llc | Process for the preparation of 2-substituted-5-(1-alkylthio)alkylpyridines |
| AR066366A1 (es) * | 2007-05-01 | 2009-08-12 | Dow Agrosciences Llc | Mezclas sinergicas plaguicidas |
| ES2369551T3 (es) * | 2007-07-20 | 2011-12-01 | Dow Agrosciences Llc | Aumento del vigor de las plantas. |
| MX2010009748A (es) * | 2008-03-03 | 2010-11-30 | Dow Agrosciences Llc | Plaguicidas. |
| CN102875548A (zh) * | 2011-07-14 | 2013-01-16 | 中国科学院大连化学物理研究所 | 一类基于肟的通过[2+2+2]环加成合成吡啶衍生物的方法 |
| EP2607343A1 (en) | 2011-12-22 | 2013-06-26 | Solvay Sa | Process for the manufacture of halogenated precursors of alkenones and of alkenones |
| DK3548466T3 (da) * | 2016-12-01 | 2022-04-19 | Syngenta Participations Ag | Fremgangsmåde til fremstilling af et mellemprodukt af pesticidaktive heterocykliske derivater med svovlindeholdende substituenter |
| WO2020139734A1 (en) * | 2018-12-27 | 2020-07-02 | Dow Agrosciences Llc | Preparation of sulfonamide herbicide process intermediates |
| CN113227052A (zh) * | 2018-12-27 | 2021-08-06 | 科迪华农业科技有限责任公司 | 磺酰胺除草剂方法中间体的制备 |
| CN115286568B (zh) * | 2022-08-24 | 2023-12-12 | 常州沃腾化工科技有限公司 | 一种2-羟基-4-三氟甲基吡啶的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2002030901A1 (en) | 2000-10-10 | 2002-04-18 | Boehringer Ingelheim Chemicals, Inc. | Process for making 3-amino-2-chloro-4-methylpyridine |
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| BE611728A (fr) * | 1960-07-12 | 1962-06-19 | American Cyanamid Co | Perfectionnements aux compositions contenant des antibiotiques à base de tétracycline |
| US3993656A (en) | 1974-11-19 | 1976-11-23 | Merck & Co., Inc. | 1,8-Naphthyridine compounds |
| JPS5221196A (en) * | 1975-08-12 | 1977-02-17 | Fujio Hashimoto | Device for removing red tide |
| JPS53121764A (en) * | 1977-03-31 | 1978-10-24 | Yamanouchi Pharmaceut Co Ltd | Heterocyclic compounds and process for their preparation |
| JPS53127490A (en) * | 1977-04-13 | 1978-11-07 | Yamanouchi Pharmaceut Co Ltd | Novel nitrogen-containing heterocyclic compound |
| JPS5384990A (en) * | 1976-12-29 | 1978-07-26 | Yamanouchi Pharmaceut Co Ltd | Novel nitrogen-containing heterocyclic compound and its preparation |
| JPS55104266A (en) * | 1979-02-02 | 1980-08-09 | Yamanouchi Pharmaceut Co Ltd | Novel pyridone derivative |
| JPS6210087A (ja) * | 1985-07-03 | 1987-01-19 | Shionogi & Co Ltd | ４，７−ジヒドロチエノ〔２，３−ｂ〕ピリジン誘導体，その製造法および循環器系疾患治療剤 |
| JPS6413065A (en) * | 1987-07-06 | 1989-01-17 | Mitsubishi Chem Ind | Peptide derivative of beta-chloro-l-(z)- dehydroglutamic acid |
| DK177191D0 (da) * | 1991-10-23 | 1991-10-23 | Novo Nordisk As | Heterocyclic compounds and their preparation and use |
| US5391745A (en) * | 1992-07-23 | 1995-02-21 | Sloan-Kettering Institute For Cancer Research | Methods of preparation of camptothecin analogs |
| PL190282B1 (pl) | 1996-09-24 | 2005-11-30 | Dow Agrosciences Llc | Związki N-([1,2,4]triazoloazynylo)benzeno-i pirydynosulfonamidowe, zawierające je kompozycje herbicydowe, pochodne chlorku pirydyno-3-sulfonylu i pochodne 2-amino[1.2.4]triazolo[1.5-c]pirymidyny |
| ATE274510T1 (de) * | 1998-06-19 | 2004-09-15 | Chiron Corp | Glycogen synthase kinase 3 inhibitoren |
| JP2004504300A (ja) * | 2000-07-18 | 2004-02-12 | ビーエーエスエフ アクチェンゲゼルシャフト | １−アリール−４−ハロアルキル−２−［１ｈ］ピリドン類 |
| US7488828B2 (en) * | 2004-06-25 | 2009-02-10 | Dow Agrosciences Llc | Process for the preparation of 4-trifluoromethyl-2(1H)-pyridinone |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002030901A1 (en) | 2000-10-10 | 2002-04-18 | Boehringer Ingelheim Chemicals, Inc. | Process for making 3-amino-2-chloro-4-methylpyridine |
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|---|---|
| CN1898255A (zh) | 2007-01-17 |
| US20070249837A1 (en) | 2007-10-25 |
| CA2550693A1 (en) | 2005-07-14 |
| IL176472A (en) | 2010-11-30 |
| CN1898255B (zh) | 2010-06-09 |
| BRPI0418047B1 (pt) | 2013-12-31 |
| ZA200605471B (en) | 2007-11-28 |
| AR046775A1 (es) | 2005-12-21 |
| ES2528716T3 (es) | 2015-02-12 |
| JP2013047245A (ja) | 2013-03-07 |
| JP2012214487A (ja) | 2012-11-08 |
| EP1723156B1 (en) | 2015-01-21 |
| CA2550693C (en) | 2013-07-30 |
| EP1723156A1 (en) | 2006-11-22 |
| JP5160092B2 (ja) | 2013-03-13 |
| AU2004309054B2 (en) | 2010-07-08 |
| IL176472A0 (en) | 2006-10-05 |
| KR20060128896A (ko) | 2006-12-14 |
| BRPI0418047A (pt) | 2007-04-17 |
| BRPI0418047B8 (pt) | 2022-06-28 |
| PL1723156T3 (pl) | 2015-07-31 |
| IN2012DN02546A (US07125994-20061024-C00024.png) | 2015-08-28 |
| IN2012DN02545A (US07125994-20061024-C00024.png) | 2015-07-17 |
| JP2007519625A (ja) | 2007-07-19 |
| DK1723156T3 (en) | 2015-04-27 |
| US7687632B2 (en) | 2010-03-30 |
| AU2004309054A1 (en) | 2005-07-14 |
| WO2005063780A1 (en) | 2005-07-14 |
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