Process for preparing 4-(cyclopropylmethoxy)-n-(3,5-dichloro-1-oxido-4-pyridyl)-5-methoxypyridine-2-carboxamide
AssigneeSanofi
InventorsJean-Paul CASIMIR, Guy ROSSEY, Christian WEHREY
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Abstract
The present invention relates to a novel process for preparing the compound 4-(cyclopropylmethoxy)-N-(3,5-di-chloro-1-oxido-4-pyridyl)-5-methoxypyridine-2-carboxamide of formula (1), in base or hydrate form or in the form of pharmaceutically acceptable salts, and also to several novel synthetic intermediates that are useful in this preparation process.
Claims12
Process for preparing 4-(cyclopropylmethoxy)-N-(3,5-dichloro-1-oxido-4-pyridyl)-5-methoxypyridine-2-carboxamide, in base or hydrate form or in the form of pharmaceutically acceptable salts, of formula 1 below:
- characterized in that it comprises:
- a step c):
- reaction of the compound 2-hydroxymethyl-5-methoxy-4-pyrid-(1H)-one of formula 5 with a methylcyclopropane derivative and a base, in a polar aprotic solvent, according to the scheme below:
- a step b):
- oxidation reaction of compound 4 obtained in step c), according to the scheme below:
- a step a):
- coupling reaction of compound 2 obtained in step b) with 3,5-dichloroaminopyridine N-oxide (compound 3) or the N-Boc derivative thereof, according to the scheme below:
Process for preparing 4-(cyclopropylmethoxy)-N-(3,5-dichloro-1-oxido-4-pyridyl)-5-methoxypyridine-2-carboxamide, in base or hydrate form or in the form of pharmaceutically acceptable salts, of formula 1 below:
- characterized in that it comprises a coupling reaction of 4-cyclopropylmethoxy-5-methoxy-2-pyridinecarboxylic acid (compound 2) with 3,5-dichloroaminopyridine N-oxide (compound 3) or the N-Boc derivative thereof, according to the scheme below:
- or N-Boc derivative of compound 3
Compound of formula 4 below:
Compound of formula 6 below:
Compound of formula 7 below:
Dependencies are inferred from the claim text.