JP2013500945A5 - - Google Patents
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- Publication number
- JP2013500945A5 JP2013500945A5 JP2012522152A JP2012522152A JP2013500945A5 JP 2013500945 A5 JP2013500945 A5 JP 2013500945A5 JP 2012522152 A JP2012522152 A JP 2012522152A JP 2012522152 A JP2012522152 A JP 2012522152A JP 2013500945 A5 JP2013500945 A5 JP 2013500945A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- mol
- dfpe
- difluoromethyl
- pyrazole
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 239000008346 aqueous phase Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XTHPZTBDQIWSFA-UHFFFAOYSA-N ethyl 5-(difluoromethyl)-1h-pyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NNC=1C(F)F XTHPZTBDQIWSFA-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 3
- MRQQMVMIANXDKC-UHFFFAOYSA-N ethyl 3-(difluoromethyl)-1-methylpyrazole-4-carboxylate Chemical compound CCOC(=O)C1=CN(C)N=C1C(F)F MRQQMVMIANXDKC-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 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 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 230000033444 hydroxylation Effects 0.000 description 2
- 238000005805 hydroxylation reaction Methods 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- CPBHXWAFWPWRPP-UHFFFAOYSA-N CCC1=C(C(=NN1)C(F)F)C#N Chemical compound CCC1=C(C(=NN1)C(F)F)C#N CPBHXWAFWPWRPP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- KDVPGBVZKTVEIS-WAYWQWQTSA-N ethyl (2z)-2-(ethoxymethylidene)-4,4-difluoro-3-oxobutanoate Chemical compound CCO\C=C(C(=O)C(F)F)/C(=O)OCC KDVPGBVZKTVEIS-WAYWQWQTSA-N 0.000 description 1
- LELJHIZDPXOEOH-UHFFFAOYSA-N ethyl 3-chloro-4,4,4-trifluoro-2-formylbut-2-enoate Chemical compound CCOC(=O)C(C=O)=C(Cl)C(F)(F)F LELJHIZDPXOEOH-UHFFFAOYSA-N 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23013409P | 2009-07-31 | 2009-07-31 | |
| US36157010P | 2010-07-06 | 2010-07-06 | |
| US61/361,570 | 2010-07-06 | ||
| US61/230,134 | 2010-07-06 | ||
| PCT/EP2010/060884 WO2011012620A2 (en) | 2009-07-31 | 2010-07-27 | Processes for the alkylation of pyrazoles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013500945A JP2013500945A (ja) | 2013-01-10 |
| JP2013500945A5 true JP2013500945A5 (enExample) | 2015-12-17 |
| JP5956334B2 JP5956334B2 (ja) | 2016-07-27 |
Family
ID=42782270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012522152A Active JP5956334B2 (ja) | 2009-07-31 | 2010-07-27 | ピラゾールのアルキル化のためのプロセス |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8563747B2 (enExample) |
| EP (1) | EP2459538B1 (enExample) |
| JP (1) | JP5956334B2 (enExample) |
| CN (1) | CN102471279A (enExample) |
| AR (1) | AR077332A1 (enExample) |
| BR (1) | BR112012008128B8 (enExample) |
| DK (1) | DK2459538T3 (enExample) |
| ES (1) | ES2525489T3 (enExample) |
| IL (1) | IL217387A (enExample) |
| MX (1) | MX2012001067A (enExample) |
| TW (1) | TW201107296A (enExample) |
| WO (1) | WO2011012620A2 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5763634B2 (ja) | 2009-07-28 | 2015-08-12 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | ピラゾールのアルキル化に関する方法 |
| PT2603494T (pt) * | 2010-08-10 | 2017-02-03 | Syngenta Participations Ag | Processo para a preparação de 3-haloalquilopirazóis |
| JP5140776B1 (ja) * | 2012-09-05 | 2013-02-13 | タマ化学工業株式会社 | １−置換−３−フルオロアルキルピラゾール−４−カルボン酸エステルの製造方法 |
| KR102540220B1 (ko) * | 2014-08-19 | 2023-06-02 | 바이엘 애니멀 헬스 게엠베하 | 헥사플루오로프로펜으로부터 5-플루오로-1h-피라졸의 제조 방법 |
| CN119823045B (zh) * | 2024-12-18 | 2025-10-17 | 湖南化工研究院有限公司 | 一种3-二氟甲基-1-甲基吡唑-4-甲酸乙酯的合成方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0759560B2 (ja) * | 1987-10-19 | 1995-06-28 | 三井東圧化学株式会社 | １，３−ジアルキルピラゾール−４−カルボン酸エステルの製造法 |
| GB9405229D0 (en) * | 1994-03-17 | 1994-04-27 | Rhone Poulenc Agriculture | Compositions of matter |
| US5498624A (en) * | 1995-05-03 | 1996-03-12 | Monsanto Company | Selected pyrazolyl derivatives |
| JP2000044541A (ja) * | 1998-08-03 | 2000-02-15 | Mitsui Chemicals Inc | １，３−ジアルキルピラゾール−４−カルボン酸エステルの製造法 |
| JP4568404B2 (ja) | 2000-05-17 | 2010-10-27 | 三井化学アグロ株式会社 | ピラゾールカルボン酸エステル誘導体の製造法 |
| DK1480955T3 (da) | 2002-03-05 | 2007-10-29 | Syngenta Participations Ag | O-cyclopropyl-carboxanilider og deres anvendelse som fungicider |
| GB0224316D0 (en) | 2002-10-18 | 2002-11-27 | Syngenta Participations Ag | Chemical compounds |
| BRPI0512118A (pt) * | 2004-06-18 | 2008-02-06 | Basf Ag | composto, processo para combater fungos nocivos, e, agente fungicida |
| TWI357898B (en) * | 2004-10-21 | 2012-02-11 | Syngenta Participations Ag | Process for the preparation of pyrazoles |
| US7863460B2 (en) * | 2005-02-25 | 2011-01-04 | Sagami Chemical Research Center | Process for producing 1-substituted-3-fluoroalkylpyrazole-4-carboxylate |
| GEP20115161B (en) | 2005-10-25 | 2011-02-10 | Syngenta Participations Ag | Heterocyclic amide derivatives useful as microbiocides |
| GB0526044D0 (en) | 2005-12-21 | 2006-02-01 | Syngenta Ltd | Novel herbicides |
| WO2008053044A2 (de) * | 2006-11-03 | 2008-05-08 | Basf Se | Hetarylcarbonsäure-n-(biphen-2-yl)amid-verbindungen |
| DK2120577T3 (en) | 2007-03-16 | 2014-12-15 | Syngenta Ltd | NOVEL SOLID FORM OF A microbicide |
| WO2008141020A1 (en) | 2007-05-11 | 2008-11-20 | Eli Lilly And Company | 2-[4-(pyrazol-4-ylalkyl)piperazin-1-yl]-3-phenyl pyrazines and pyridines and 3-[4-(pyrazol-4-ylalkyl)piperazin-1-yl]-2-phenyl pyridines as 5-ht7 receptor antagonists |
| RU2459807C2 (ru) * | 2007-05-31 | 2012-08-27 | Зингента Партисипейшнс Аг | Способ получения пиразолов |
| KR20110004903A (ko) | 2008-05-08 | 2011-01-14 | 바스프 에스이 | 아릴카르복스아미드의 제조 방법 |
| GB0812028D0 (en) | 2008-07-01 | 2008-08-06 | Syngenta Participations Ag | Fungicidal compositions |
-
2010
- 2010-07-27 CN CN2010800339701A patent/CN102471279A/zh active Pending
- 2010-07-27 US US13/388,246 patent/US8563747B2/en active Active
- 2010-07-27 DK DK10736729.4T patent/DK2459538T3/en active
- 2010-07-27 MX MX2012001067A patent/MX2012001067A/es not_active Application Discontinuation
- 2010-07-27 ES ES10736729.4T patent/ES2525489T3/es active Active
- 2010-07-27 AR ARP100102714A patent/AR077332A1/es unknown
- 2010-07-27 JP JP2012522152A patent/JP5956334B2/ja active Active
- 2010-07-27 TW TW099124617A patent/TW201107296A/zh unknown
- 2010-07-27 BR BR112012008128A patent/BR112012008128B8/pt active IP Right Grant
- 2010-07-27 EP EP10736729.4A patent/EP2459538B1/en active Active
- 2010-07-27 WO PCT/EP2010/060884 patent/WO2011012620A2/en not_active Ceased
-
2012
- 2012-01-05 IL IL217387A patent/IL217387A/en active IP Right Grant
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