WO2018201272A1 - Procédé de production d'acides carboxyliques ou de dérivés d'acide carboxylique - Google Patents

Procédé de production d'acides carboxyliques ou de dérivés d'acide carboxylique Download PDF

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Publication number
WO2018201272A1
WO2018201272A1 PCT/CN2017/082689 CN2017082689W WO2018201272A1 WO 2018201272 A1 WO2018201272 A1 WO 2018201272A1 CN 2017082689 W CN2017082689 W CN 2017082689W WO 2018201272 A1 WO2018201272 A1 WO 2018201272A1
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WO
WIPO (PCT)
Prior art keywords
group
compound
alkyl
process according
optionally substituted
Prior art date
Application number
PCT/CN2017/082689
Other languages
English (en)
Inventor
Mingchun WANG
Qingyi Li
Jaunzems JANIS
Original Assignee
Solvay Fluor Gmbh
Changzhou Keylab Biochemical Co., Ltd.
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.)
Filing date
Publication date
Application filed by Solvay Fluor Gmbh, Changzhou Keylab Biochemical Co., Ltd. filed Critical Solvay Fluor Gmbh
Priority to PCT/CN2017/082689 priority Critical patent/WO2018201272A1/fr
Priority to PCT/EP2018/061139 priority patent/WO2018202677A1/fr
Publication of WO2018201272A1 publication Critical patent/WO2018201272A1/fr

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Classifications

    • 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

Definitions

  • Agrochemical active ingredients which contain 3-halomethylpyrazol-4-yl building blocks are, for example, 2’- [1, 1’-bicycloprop-2-yl] -3- (difluoromethyl) -1-methylpyrazole-4-carboxanilide (Sedaxane) , as described, for example, in WO2006015866, 3- (difluoromethyl) -1-methyl-N- [2- (3’, 4’, 5’-trifluorophenyl) phenyl] pyrazole-4-carboxamide (Fluxapyroxad) , as described, for example, in WO2006087343, N- (3′, 4′-Dichloro-5-fluorobiphenyl-2-yl) -3- (difluoromethyl) -1-
  • WO2016/152886 discloses oxidation of pyrazolyl ketone derivatives with hypohalite solutions.
  • hypohalites When hypohalites are used for oxidation of the keto function, a large amount, at least three equivalents, of hypohalite is necessary to convert the keto group into a carboxylate salt. This results in a large volume of salt waste per mole carboxylate produced, which is often also difficult to treat because of its organic impurities.
  • hypohalite solutions are often restricted in their upper concentration limit due to stability concerns, the waste volume is even higher per mole carboxylate produced.
  • the invention further concerns a process as shown above wherein the process for the manufacture of a compound of formula (II) further comprises a step of reacting a compound of formula (III) with a compound selected from the group consisting of compound (IV) , (V) and (VI) to obtain the compound of formula (I)
  • catalytic oxidation is intended to denote an oxidation wherein the oxidation is carried out in the presence of at least one oxidant and at least one catalyst. Oxidants and catalysts will be defined as below.
  • the invention concerns a process for the manufacture of a compound of formula (II) comprising a step of catalytic oxidation in the presence of at least one catalyst and at least one oxidant, of compound number (I) ,
  • R 3 is selected from the group consisting of H, X, COOR, OR, SR, C (O) NR 2 , wherein R is selected from the group consisting of hydrogen, a C 1 -C 12 -alkyl, CN, C 2 -C 6 alkenyl, aryl, C 3 -C 8 cycloalkyl, aralkyl or heteroaryl group, each of which is optionally substituted, with the proviso that both R in C (O) NR 2 may be the same or different, wherein X is a halogen atom and is selected from the group consisting of F, Cl, Br and I, and R is independently selected from the group consisting of hydrogen or a C 1 -C 12 -alkyl, C 2 -C 6 alkenyl, aryl, cycloalkyl, aralkyl, heteroaryl,
  • aryl group intends to denote C 5 -C 18 monocyclic and polycyclic aromatic hydrocarbons with 5 to 18 carbon atoms in the cyclic system. Specifically, this definition comprises, for example, the meanings cyclopentadienyl, phenyl, cycloheptatrienyl, cyclooctatetraenyl, naphthyl and anthracenyl.
  • a C 1 -C 4 alkyl group, C 1 -C 8 alkyl group, C 1 -C 12 alkyl group, aryl group, heteroaryl group, C 1 -C 12 -alkyl group, C 2 -C 6 alkenyl group, aryl group, aralkyl group or heteroaryl group each can be optionally substituted by one or more substituents of the following group consisting of R', -X', -OR', -SR', -NR' 2 , -SiR' 3 , -COOR', - (C-O) R', -CN and -CONR' 2 , wherein R’is selected independently, from the group consisting of hydrogen or C 1 -C 12 -alkyl group and X'is selected from the group consisting of F, Cl, Br, or I.
  • R 2 is selected from the group consisting of an optionally substituted C 1 -C 8 alkyl group, an optionally substituted C 3 -C 8 cycloalkyl group, an optionally substituted aryl group and an optionally substituted heteroaryl group.
  • Preferred R 2 are ethyl, methyl and phenyl, wherein a methyl group is most preferred as R 2 .
  • the at least one catalyst often is selected from the group consisting of a metal salt comprising at least one metal species and a metal complex comprising at least one metal species.
  • metal species intends to denote a metal atom with charge zero or a positive charge of one, two, three or up to seven, depending on the valency in the respective catalyst compound. In some catalyst compounds, more than one metal species can be present, but generally, the catalyst is preferred to have one metal species present.
  • the catalyst compound is a metal salt
  • the at least one metal species often is a cation with a positive charge of one, two, three, four, five, six or seven.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention concerne un procédé de fabrication d'acides carboxyliques ou de dérivés d'acide carboxylique et un procédé de fabrication de composés actifs sur les plans agrochimique et pharmaceutique comprenant le procédé de fabrication d'acides carboxyliques ou de leurs dérivés. Le procédé de fabrication d'acides carboxyliques ou de dérivés d'acide carboxylique comprend une étape d'oxydation catalytique en présence d'au moins un catalyseur et d'au moins un oxydant, du composés numéro (I) pour obtenir un composé de formule (II).
PCT/CN2017/082689 2017-05-02 2017-05-02 Procédé de production d'acides carboxyliques ou de dérivés d'acide carboxylique WO2018201272A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/CN2017/082689 WO2018201272A1 (fr) 2017-05-02 2017-05-02 Procédé de production d'acides carboxyliques ou de dérivés d'acide carboxylique
PCT/EP2018/061139 WO2018202677A1 (fr) 2017-05-02 2018-05-02 Procédé de production d'acides carboxyliques ou de dérivés d'acide carboxylique

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2017/082689 WO2018201272A1 (fr) 2017-05-02 2017-05-02 Procédé de production d'acides carboxyliques ou de dérivés d'acide carboxylique

Publications (1)

Publication Number Publication Date
WO2018201272A1 true WO2018201272A1 (fr) 2018-11-08

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PCT/CN2017/082689 WO2018201272A1 (fr) 2017-05-02 2017-05-02 Procédé de production d'acides carboxyliques ou de dérivés d'acide carboxylique
PCT/EP2018/061139 WO2018202677A1 (fr) 2017-05-02 2018-05-02 Procédé de production d'acides carboxyliques ou de dérivés d'acide carboxylique

Family Applications After (1)

Application Number Title Priority Date Filing Date
PCT/EP2018/061139 WO2018202677A1 (fr) 2017-05-02 2018-05-02 Procédé de production d'acides carboxyliques ou de dérivés d'acide carboxylique

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117384096A (zh) * 2023-12-13 2024-01-12 山东国邦药业有限公司 一种二氟吡唑酸的制备方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3952950A1 (fr) 2019-04-08 2022-02-16 Amgen Inc. Dispositif automatisé de délivrance de médicaments et conteneur

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CN104945325A (zh) * 2015-06-19 2015-09-30 浙江永太科技股份有限公司 一种吡唑甲酸衍生物的制备方法
CN105541716A (zh) * 2015-03-26 2016-05-04 旭硝子株式会社 吡唑衍生物的制造方法
KR20170017372A (ko) * 2015-08-06 2017-02-15 (주)부흥산업사 피라졸 카르복실산 유도체의 제조방법
CN106554310A (zh) * 2015-09-25 2017-04-05 陈旭 一种3-二氟甲基-1-甲基吡唑-4-甲酸的合成方法

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Publication number Priority date Publication date Assignee Title
DE10215292A1 (de) 2002-02-19 2003-08-28 Bayer Cropscience Ag Disubstitutierte Pyrazolylcarbocanilide
GB0224316D0 (en) 2002-10-18 2002-11-27 Syngenta Participations Ag Chemical compounds
GB0418048D0 (en) 2004-08-12 2004-09-15 Syngenta Participations Ag Method for protecting useful plants or plant propagation material
DE102005007160A1 (de) 2005-02-16 2006-08-24 Basf Ag Pyrazolcarbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen
CN101962364B (zh) 2005-09-16 2013-01-09 先正达参股股份有限公司 酰胺的制备方法
AU2006308128B2 (en) 2005-10-25 2011-07-28 Syngenta Participations Ag Heterocyclic amide derivatives useful as microbiocides
US8987470B2 (en) 2010-10-27 2015-03-24 Solvay Sa Process for the preparation of pyrazole-4-carboxamides
WO2017054112A1 (fr) 2015-09-28 2017-04-06 常州市卜弋科研化工有限公司 Procédé de préparation d'acide 3-fluoroalkyl-1-méthylpyrazole-4-carboxylique

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105541716A (zh) * 2015-03-26 2016-05-04 旭硝子株式会社 吡唑衍生物的制造方法
CN104945325A (zh) * 2015-06-19 2015-09-30 浙江永太科技股份有限公司 一种吡唑甲酸衍生物的制备方法
KR20170017372A (ko) * 2015-08-06 2017-02-15 (주)부흥산업사 피라졸 카르복실산 유도체의 제조방법
CN106554310A (zh) * 2015-09-25 2017-04-05 陈旭 一种3-二氟甲基-1-甲基吡唑-4-甲酸的合成方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117384096A (zh) * 2023-12-13 2024-01-12 山东国邦药业有限公司 一种二氟吡唑酸的制备方法

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