Method of synthesis of ferroquine by convergent reductive amination
AssigneeSanofi
InventorsVincent FEREY, Julia MATEOS-CARO, Regis MONDIERE, Philippe VAYRON, Sylvie VIGNE
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Abstract
The invention relates to a method of synthesis of ferroquine of formula (F) or of its metabolite of formula (Fm): comprising a reaction of reductive amination, said reaction comprising: (i) a stage of condensation of an aldehyde-amino ferrocene of formula (III), in which R represents a hydrogen atom or a methyl group, with 7-chloroquinolin-4-amine as shown below, followed by (ii) a stage of reduction of the product of condensation obtained in the preceding stage and (iii) then a stage of hydrolysis of the reaction mixture in the presence of an aqueous solution of ammonia or of citric acid.
Claims21
A method of synthesis of ferroquine of formula (F) or of its metabolite of formula (Fm):
- comprising a reaction of reductive amination in a reaction solvent, in which reaction:
- (i) an aldehyde-amino ferrocene of formula (III),
- in which R represents a hydrogen atom or a methyl group, is condensed with 7-chloroquinolin-4-amine
- (ii) the product of condensation thus obtained of formula (II),
- with R representing a hydrogen atom or a methyl group, is reduced in the presence of metal hydride, and
- (iii) the reaction mixture is hydrolyzed prior to isolation of the ferroquine of formula (F) or of its metabolite of formula (Fm).
Dependencies are inferred from the claim text.