WO2019215076A1 - Procédé de préparation d'hétérocycles contenant de l'azote - Google Patents

Procédé de préparation d'hétérocycles contenant de l'azote Download PDF

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Publication number
WO2019215076A1
WO2019215076A1 PCT/EP2019/061535 EP2019061535W WO2019215076A1 WO 2019215076 A1 WO2019215076 A1 WO 2019215076A1 EP 2019061535 W EP2019061535 W EP 2019061535W WO 2019215076 A1 WO2019215076 A1 WO 2019215076A1
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WO
WIPO (PCT)
Prior art keywords
formula
compounds
alkyl
series
rest
Prior art date
Application number
PCT/EP2019/061535
Other languages
German (de)
English (en)
Inventor
Peter Jeschke
Sergii Pazenok
Original Assignee
Bayer Aktiengesellschaft
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 Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Publication of WO2019215076A1 publication Critical patent/WO2019215076A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to an improved process for the preparation of nitrogen-containing heterocyclic compounds of formula (I) shown below.
  • X is a radical selected from halogen, cyano (CN), nitro, alkyl, alkoxy, alkylthio, alkylsulfoxyl, alkylsulfonyl, haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfonyl, alkoxycarbonyl, alkylcarbonyl, cycloalkylcarbonyl, m is a number from the series 0, 1 and 2 stands,
  • Y is a radical selected from halogen, cyano, nitro, amino, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfoxyl,
  • X is a radical from the series halogen, cyano, nitro, Ci-C t -alkyl, C t -alkoxy, C t alkylthio, Ci-C t alkylsulfoxyl, Ci-C t alkylsulfonyl, halogen Ci-C 4 alkyl, halogen-Ci-C 4 alkoxy, halo-Ci-C4-alkylthio, halo-Ci-C4-alkylsulfonyl, Ci-C 4 alkoxycarbonyl, C 1 -C 4 - alkylcarbonyl, and C 3 -C 6 -cycloalkylcarbonyl, m is a number from the series 0, 1 and 2,
  • A-1 stands, and
  • B 3 is and Y 2 is a radical from the series, difluoromethyl, trifluoromethyl, difluorochloromethyl, difluorbrommethyl, 2,2-difluoroethyl and 2,2,2-trifluoroethyl.
  • the reaction step 1 is usually carried out in a temperature range of 20 ° C to 120 ° C and optionally in the presence of a solvent or diluent. Preferably, the reaction is carried out at about 80 ° C without solvent or diluent.
  • the compounds of the formula (III) are reacted by reaction with alkyl thiolates of the formula (IV) to give compounds of the formula (V).
  • the molar ratio of the alkylthiolate (IV) to the halogen compound of the formula (III) may be in the range of about 6 to about 1. Preferably, it is in the range of about 4.5 to about 1.5, more preferably in the range of about 3.5 to 2.
  • the use of larger amounts of alkyl thiolate (IV) is basically possible, but generally uneconomical.
  • the solvent or diluent is separated off and the remaining residue is stirred with water.
  • the compounds of the formula (I) can then be isolated, for example by separating off the precipitated crystals (cf. Preparation Example 1) or by chromatographic purification.
  • the process according to the invention can be carried out in a preferred embodiment as a one-pot process.
  • the intermediates of the formulas (III) and (V) are not isolated and optionally purified. It is also possible to carry out the process so as to isolate the intermediate of the formula (III), but not the intermediate of the formula (V). It is also possible to carry out the process in such a way that the intermediate of the formula (III) is not isolated, but the intermediate of the formula (V) is.
  • Step 1 Synthesis of compounds of the formula (III) 2-chloro-1- (6-difluoromethyl-pyridin-3-yl) -pyridinium chloride (III-2)

Abstract

La présente invention concerne un procédé amélioré de préparation de composés hétérocycliques contenant de l'azote, représentés par la formule (I).
PCT/EP2019/061535 2018-05-08 2019-05-06 Procédé de préparation d'hétérocycles contenant de l'azote WO2019215076A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP18171126.8 2018-05-08
EP18171126 2018-05-08

Publications (1)

Publication Number Publication Date
WO2019215076A1 true WO2019215076A1 (fr) 2019-11-14

Family

ID=62142953

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2019/061535 WO2019215076A1 (fr) 2018-05-08 2019-05-06 Procédé de préparation d'hétérocycles contenant de l'azote

Country Status (2)

Country Link
TW (1) TW201946902A (fr)
WO (1) WO2019215076A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11697666B2 (en) 2021-04-16 2023-07-11 Gilead Sciences, Inc. Methods of preparing carbanucleosides using amides
US11767337B2 (en) 2020-02-18 2023-09-26 Gilead Sciences, Inc. Antiviral compounds

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001090071A2 (fr) * 2000-05-19 2001-11-29 Bayer Cropscience Ag Iminoazines substituees
WO2007131179A1 (fr) * 2006-05-05 2007-11-15 Millennium Pharmaceuticals, Inc. INHIBITEURS DE FACTEUR Xa
WO2017005673A1 (fr) 2015-07-06 2017-01-12 Bayer Cropscience Aktiengesellschaft Hétérocycles contenant de l'azote utiles en tant que pesticides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001090071A2 (fr) * 2000-05-19 2001-11-29 Bayer Cropscience Ag Iminoazines substituees
WO2007131179A1 (fr) * 2006-05-05 2007-11-15 Millennium Pharmaceuticals, Inc. INHIBITEURS DE FACTEUR Xa
WO2017005673A1 (fr) 2015-07-06 2017-01-12 Bayer Cropscience Aktiengesellschaft Hétérocycles contenant de l'azote utiles en tant que pesticides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11767337B2 (en) 2020-02-18 2023-09-26 Gilead Sciences, Inc. Antiviral compounds
US11697666B2 (en) 2021-04-16 2023-07-11 Gilead Sciences, Inc. Methods of preparing carbanucleosides using amides

Also Published As

Publication number Publication date
TW201946902A (zh) 2019-12-16

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