MX344084B - Procedimiento para la síntesis regioselectiva de derivados de ácido 1-alquil-3-haloalquil-pirazol-4-carboxílico. - Google Patents
Procedimiento para la síntesis regioselectiva de derivados de ácido 1-alquil-3-haloalquil-pirazol-4-carboxílico.Info
- Publication number
- MX344084B MX344084B MX2015009067A MX2015009067A MX344084B MX 344084 B MX344084 B MX 344084B MX 2015009067 A MX2015009067 A MX 2015009067A MX 2015009067 A MX2015009067 A MX 2015009067A MX 344084 B MX344084 B MX 344084B
- Authority
- MX
- Mexico
- Prior art keywords
- acid derivatives
- alkyl
- carboxylic acid
- pyroazole
- haloalkylâ
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- -1 2,3-disubstituted acrylic acid Chemical class 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 150000007857 hydrazones Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/74—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/76—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/10—Hydrazines
- C07C243/12—Hydrazines having nitrogen atoms of hydrazine groups bound to acyclic carbon atoms
- C07C243/16—Hydrazines having nitrogen atoms of hydrazine groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C243/18—Hydrazines having nitrogen atoms of hydrazine groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/74—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/78—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
- C07C251/80—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
La presente invención se refiere a un procedimiento para la síntesis regioselectiva de derivados de ácido 1-alquil-3-haloalquil-pirazol-4-carboxílico mediante ciclación de derivados de ácido acrílico 2,3-disustituidos, así como a las hidrazonas formadas en el procedimiento como productos intermedios.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08151891A EP2133341A1 (de) | 2008-02-25 | 2008-02-25 | Verfahren zur regioselektiven Synthese von 1-Alkyl-3-haloalkyl-pyrazol-4-carbonsäure-Derivaten |
| PCT/EP2009/000958 WO2009106230A2 (de) | 2008-02-25 | 2009-02-12 | Verfahren zur regioselektiven synthese von 1-alkyl-3-haloalkyl-pyrazol-4-carbonsäur e-derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX344084B true MX344084B (es) | 2016-12-05 |
Family
ID=39590527
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2010008553A MX2010008553A (es) | 2008-02-25 | 2009-02-12 | Procedimiento para la sintesis regioselectiva de derivados de acido 1-alquil-3-haloalquil-pirazol-4-carboxilico. |
| MX2015009067A MX344084B (es) | 2008-02-25 | 2009-02-12 | Procedimiento para la síntesis regioselectiva de derivados de ácido 1-alquil-3-haloalquil-pirazol-4-carboxílico. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2010008553A MX2010008553A (es) | 2008-02-25 | 2009-02-12 | Procedimiento para la sintesis regioselectiva de derivados de acido 1-alquil-3-haloalquil-pirazol-4-carboxilico. |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US8629288B2 (es) |
| EP (2) | EP2133341A1 (es) |
| JP (2) | JP5756293B2 (es) |
| KR (1) | KR101656690B1 (es) |
| CN (2) | CN104277001A (es) |
| BR (2) | BRPI0908891A2 (es) |
| CA (1) | CA2716381C (es) |
| DK (1) | DK2247577T4 (es) |
| ES (1) | ES2561038T5 (es) |
| IL (1) | IL207151A0 (es) |
| MX (2) | MX2010008553A (es) |
| MY (2) | MY170036A (es) |
| RU (2) | RU2498977C9 (es) |
| TW (1) | TWI458712B (es) |
| WO (1) | WO2009106230A2 (es) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009021987A1 (en) | 2007-08-16 | 2009-02-19 | Solvay (Société Anonyme) | Process for the preparation of esters of 4-fluorosubstituted 3-oxo-alcanoic acids |
| EP2133341A1 (de) * | 2008-02-25 | 2009-12-16 | Bayer CropScience AG | Verfahren zur regioselektiven Synthese von 1-Alkyl-3-haloalkyl-pyrazol-4-carbonsäure-Derivaten |
| EP2100883A1 (de) * | 2008-03-10 | 2009-09-16 | Bayer CropScience AG | Verfahren zur regioselektiven Synthese von 1-Alkyl-3-haloalkyl-pyrazol-4carbonsäure-Derivaten |
| AU2009243550B2 (en) * | 2008-05-05 | 2014-06-26 | Basf Se | Method for preparing 1,3,4-substituted pyrazol compounds |
| BR112013032988A2 (pt) | 2011-06-21 | 2016-08-16 | Bayer Ip Gmbh | método para a produção de pirazolilcarboxanilidas |
| US9012657B2 (en) | 2011-06-22 | 2015-04-21 | Central Glass Company, Limited | Method for producing pyrazole compound |
| EP2623496A1 (de) | 2012-02-01 | 2013-08-07 | Bayer CropScience AG | Verfahren zur Herstellung von 3,5-bis (fluoralkyl)-pyrazol-4-carbonsäure-Derivaten und 3,5-bis(fluoralkyl)-pyrazolen |
| EP2644598A1 (en) | 2012-03-30 | 2013-10-02 | Solvay Sa | Method for the manufacture of heterocycles |
| EP2644593A1 (en) * | 2012-03-30 | 2013-10-02 | Solvay Sa | Dialkoxymethyl oxobutyric acid esters, their manufacture and use |
| CN104284879A (zh) | 2012-05-16 | 2015-01-14 | 索尔维公司 | 1-取代甲叉基化合物的制备 |
| EP2671873A1 (en) | 2012-06-06 | 2013-12-11 | Solvay Sa | Method for the cyclization of hydrazinoacrylic acid derivatives |
| EP2671874B1 (en) | 2012-06-06 | 2016-01-13 | Solvay Sa | Preparation of esters of 1-substituted-3-fluoroalkyl-pyrazole-4-carboxylic acids |
| US8871947B2 (en) | 2013-02-04 | 2014-10-28 | KingChem LLC | Preparation of alkyl 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid ester |
| BR112015028751B1 (pt) | 2013-05-22 | 2021-01-12 | Bayer Cropscience Aktiengesellschaft | Processo para a preparação de derivados de 3,5-bis (fluoralquil)pirazol a partir de alfa, alfa-dihaloaminas e uso destes para preparação de ingredientes fungicidas ativos |
| KR102233203B1 (ko) | 2013-05-22 | 2021-03-26 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 3,5-비스(플루오로알킬)피라졸 유도체의 제조방법 |
| CN103360313A (zh) * | 2013-07-12 | 2013-10-23 | 雅本化学股份有限公司 | 3-氟代烷基-1-取代吡唑-4-羧酸及其制备方法 |
| TWI647215B (zh) | 2013-11-11 | 2019-01-11 | 德商拜耳作物科學股份有限公司 | 自α,α-二鹵胺製備3,5-雙鹵烷基吡唑衍生物之方法 |
| WO2015085464A1 (en) | 2013-12-09 | 2015-06-18 | King Chem, Llc | Process for preparing alkyl 3-difluoromethyl-1-methyl-1h-pyrazole-4-carboxylate and its analogs |
| EP3015458A1 (en) | 2014-11-03 | 2016-05-04 | Bayer CropScience AG | Process for preparing 3,5-bis(haloalkyl)pyrazole derivatives from a,a-dihaloamines and ketimines |
| ES2663614T3 (es) * | 2014-03-24 | 2018-04-16 | Bayer Cropscience Aktiengesellschaft | Procedimiento de preparación de derivados de 3,5-bis(haloalquil)pirazol a partir de alfa, alfa-dihaloaminas y cetiminas |
| WO2015189141A1 (en) | 2014-06-11 | 2015-12-17 | Bayer Cropscience Ag | Process for preparing 3,5-bis(haloalkyl)pyrazole derivatives via acylation of hydrazones |
| DK3154947T3 (en) | 2014-06-11 | 2018-06-18 | Bayer Cropscience Ag | PROCEDURE FOR PREPARING 3,5-BIS (HALOGENAL COOL) PYRAZOLES BY ACYLATION OF KETIMINES |
| CN105541716B (zh) | 2015-03-26 | 2024-02-23 | Agc株式会社 | 吡唑衍生物的制造方法 |
| EP3313820A1 (en) | 2015-06-26 | 2018-05-02 | Bayer CropScience Aktiengesellschaft | Process for preparing substituted pyrazoles containing haloalkoxy- and haloalkylthio groups from , -dihaloalkylamines and ketimines |
| CN106467492B (zh) * | 2015-08-14 | 2019-12-17 | 联化科技(盐城)有限公司 | 多氟甲基吡唑类化合物的制备方法、中间体及制备方法 |
| EP3416949A1 (en) * | 2016-02-18 | 2018-12-26 | Solvay Sa | Process for the manufacture of carboxamides |
| WO2018024644A1 (en) | 2016-08-02 | 2018-02-08 | Solvay Sa | Manufacture of hydrazinyl compounds useful in the manufacture of pyrazole carboxylic acid and derivatives, hydrazinyl compounds and their use |
| ES2849960T3 (es) | 2016-09-21 | 2021-08-24 | Bayer Cropscience Ag | Procedimiento para la preparación de 3-fluoroalquil-5-pirazolcarboxilatos y ácidos 3-fluoroalquil-5-pirazolcarboxílicos |
| CN111587241A (zh) * | 2017-12-22 | 2020-08-25 | 索尔维公司 | 亚胺鎓化合物的制造方法及其在制造吡唑衍生物中的应用 |
| WO2019122164A1 (en) | 2017-12-22 | 2019-06-27 | Solvay Sa | Process for the manufacture of pyrazole carboxylic derivatives and precursors thereof |
| MX2020013769A (es) | 2018-06-18 | 2021-03-02 | Bayer Ag | Carboxilatos de 3-pirazol disustituidos y un proceso para su preparacion mediante la acilacion de enolatos. |
| WO2020093715A1 (en) | 2018-11-07 | 2020-05-14 | Fujian Yongjing Technology Co., Ltd | New process for manufacture of pyrazoles or pyrimidones |
| CN112480007B (zh) * | 2020-12-08 | 2022-11-18 | 宿迁市科莱博生物化学有限公司 | 一种1,3-二甲基-1h-吡唑-4-羧酸的合成方法 |
| CN114195678A (zh) * | 2021-12-24 | 2022-03-18 | 江苏七洲绿色科技研究院有限公司 | 一种中间体、其制备方法及用其制备3-二氟甲基-1-甲基吡唑-4-甲酸乙酯的方法 |
| CN114195715B (zh) * | 2021-12-31 | 2024-05-10 | 福建永晶科技股份有限公司 | 1-甲基-3-二氟甲基-4-吡唑酸和1-甲基-3-三氟甲基-4-吡唑酸的制备方法 |
| CN117447401B (zh) * | 2023-12-26 | 2024-04-19 | 山东国邦药业有限公司 | 一种二氟吡唑酸的合成方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20000035081A (ko) | 1998-11-10 | 2000-06-26 | 마크 에스. 아들러 | 2-(트리할로아세틸)-3-(치환된 아미노)-2-프로페노에이트 제조방법 |
| DE10215292A1 (de) | 2002-02-19 | 2003-08-28 | Bayer Cropscience Ag | Disubstitutierte Pyrazolylcarbocanilide |
| DE10349500A1 (de) * | 2003-10-23 | 2005-06-02 | Bayer Cropscience Ag | Verfahren zum Herstellen von 2-Dihalogenacyl-3-amino-acrylsäureestern und 3-Dihalogenmethyl-pyrazol-4-carbonsäureestern |
| AU2005298922B2 (en) * | 2004-10-21 | 2012-01-19 | Syngenta Participations Ag | Process for the preparation of pyrazoles |
| JP4114754B2 (ja) | 2005-02-25 | 2008-07-09 | 財団法人相模中央化学研究所 | 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 |
| DE102006039909A1 (de) | 2006-08-25 | 2008-03-13 | Bayer Cropscience Ag | Verfahren zum Herstellen von 3-Dihalomethyl-pyrazol-4-carbonsäurederivaten |
| DE102007005296A1 (de) | 2007-02-02 | 2008-08-07 | Bayer Cropscience Ag | Verfahren zum Herstellen von Dihaloacetessigsäurealkylestern |
| EP2008996A1 (en) * | 2007-06-27 | 2008-12-31 | Syngeta Participations AG | Process for the production of pyrazoles |
| EP2133341A1 (de) * | 2008-02-25 | 2009-12-16 | Bayer CropScience AG | Verfahren zur regioselektiven Synthese von 1-Alkyl-3-haloalkyl-pyrazol-4-carbonsäure-Derivaten |
| EP2100883A1 (de) * | 2008-03-10 | 2009-09-16 | Bayer CropScience AG | Verfahren zur regioselektiven Synthese von 1-Alkyl-3-haloalkyl-pyrazol-4carbonsäure-Derivaten |
| AU2009243550B2 (en) * | 2008-05-05 | 2014-06-26 | Basf Se | Method for preparing 1,3,4-substituted pyrazol compounds |
-
2008
- 2008-02-25 EP EP08151891A patent/EP2133341A1/de not_active Ceased
-
2009
- 2009-02-12 BR BRPI0908891-1A patent/BRPI0908891A2/pt not_active Application Discontinuation
- 2009-02-12 ES ES09715350T patent/ES2561038T5/es active Active
- 2009-02-12 CN CN201410483954.2A patent/CN104277001A/zh active Pending
- 2009-02-12 JP JP2010547083A patent/JP5756293B2/ja active Active
- 2009-02-12 MY MYPI2015000498A patent/MY170036A/en unknown
- 2009-02-12 US US12/919,365 patent/US8629288B2/en active Active
- 2009-02-12 KR KR1020107020058A patent/KR101656690B1/ko active Active
- 2009-02-12 MX MX2010008553A patent/MX2010008553A/es active IP Right Grant
- 2009-02-12 CA CA2716381A patent/CA2716381C/en active Active
- 2009-02-12 WO PCT/EP2009/000958 patent/WO2009106230A2/de not_active Ceased
- 2009-02-12 MY MYPI2010003885A patent/MY156546A/en unknown
- 2009-02-12 EP EP09715350.6A patent/EP2247577B2/de active Active
- 2009-02-12 RU RU2010139278/04A patent/RU2498977C9/ru active
- 2009-02-12 BR BR122016027233-8A patent/BR122016027233B1/pt active IP Right Grant
- 2009-02-12 MX MX2015009067A patent/MX344084B/es unknown
- 2009-02-12 CN CN200980106024.2A patent/CN102026981B/zh active Active
- 2009-02-12 DK DK09715350.6T patent/DK2247577T4/da active
- 2009-02-24 TW TW098105720A patent/TWI458712B/zh active
-
2010
- 2010-07-22 IL IL207151A patent/IL207151A0/en active IP Right Grant
-
2013
- 2013-03-14 US US13/803,622 patent/US8592605B2/en active Active
- 2013-07-24 RU RU2013134651A patent/RU2661192C2/ru active
-
2014
- 2014-11-07 JP JP2014227243A patent/JP2015071615A/ja active Pending
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