R. Vaid, Jeremy T. Spitler, Sathish K. Boini
Jul 1, 2012
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Synthesis
Abstract
A practical synthesis of the title compound was accomplished by hydrogenation of 2-{4-[4-fluoro-3-(trifluoromethyl)phenyl]-2-(pyridin-4-yl)-1 H -imidazol-1-yl}- N , N -dimethylethanamine. The latter was obtained by N-alkylation of 4-{4-[4-fluoro-3-(trifluoromethyl)phenyl]-1 H -imidazol-2-yl}pyridine. Treatment of N -{2-[4-fluoro-3-(trifluoromethyl)phenyl]-2-oxoethyl}isonicotinamide hydrochloride with ammonium acetate in acetic acid provided 4-{4-[4-fluoro-3-(trifluoromethyl)phenyl]-1 H -imidazol-2-yl}pyridine. Coupling of 2-amino-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethanone 4-methylbenzene sulfonate with pyridine 4-carboxylic acid using either T 3 P or EDCI-HOBt provided N -{2-[4-fluoro-3-(trifluoromethyl)phenyl]-2-oxoethyl}isonicotinamide hydrochloride.