Method for preparing 2-chloro-n-(1-cyanocyclopropyl)-5-[2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′h-1,3′-bipyrazol-4-yl]benzamide
AssigneeVetoquinol SA
InventorsFranz-Josef Mais, Werner Lindner, Britta Olenik, Birgit Keil, Hildegard Scheithauer
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Abstract
The present invention relates to a method for preparing 2-chloro-N-(1-cyanocyclopropyl)-5-[2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]benzamide, i.e. the compound of the formula (I) and to a method for purifying the compound of the formula I. The present invention additionally relates to new crystal forms of the compound of the formula I.
Claims13
A method for preparing a compound of formula (I)
- by reacting a compound of formula (VI)
- where
- A is a boron-containing substituent selected from the group consisting of:
- a boronic acid radical of the formula
- a trifluoroborate of the formula
- -BF3M,
- where M is an alkali metal salt,
- and a boronic ester of the formula
- where R1 and R2 are independently C1-C6 alkyl or C3-C6 cycloalkyl, or R1 and R2 together form a C1-C6 alkylene group optionally substituted by one or more C1-C4 alkyl groups,
- with a compound of formula (VII)
- where X is a reactive group selected from:
- bromine, iodine and a radical —O—SO2—Y, where Y is C1-C8 perfluoroalkyl,
- in the presence of a base and a catalyst,
- wherein compound VI is used in amounts of 0.7 to 1.3 equivalents based on the structural unit of the formula VII;
- wherein the base[s] used are alkali metal carbonates, alkaline earth metal carbonates, alkali metal hydrogen carbonates, alkaline earth metal hydrogen carbonates, alkali metal phosphates, alkaline earth metal phosphates, alkali metal fluorides, or mixtures thereof and is used in an amount of 1 to 10 equivalents based on the starting material of the formula VI.
A method for purifying the compound of formula I, wherein the compound is the crystallized form of a compound of formula (I) modification I, the method comprising:
- crystallizing the compound from an aromatic hydrocarbon, wherein the aromatic hydrocarbon is selected from the group consisting of toluene, ethylbenzene, ortho-xylene, meta-xylene, and para-xylene.
A crystalline form of a compound of formula (I) modification I.
Dependencies are inferred from the claim text.