Sodium cyanoborohydride → HCID 57666422, compound

Participants

Reaction Steps

A solution of sodium cyanoborohydride in tetrahydrofuran (1 M, 6 mL) was added to a solution of N-{4-[4-amino-6,7-dimethyl-2-({[(1-methylethylidene)amino]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]butyl}benzamide (260 mg, 0.62 mmol) in 1:2 acetic acid/methanol (9 mL). The reaction mixture was stirred overnight, concentrated under reduced pressure, and partitioned between 1 M aqueous hydrochloric acid (20 mL) and chloroform (5 mL). After the bubbling subsided, the layers were separated and the aqueous phase was washed with chloroform (2×5 mL). The organic layers were combined and back-extracted with 1 M aqueous hydrochloric acid (2×5 mL). The aqueous layers were combined and adjusted to pH 10 with 1 M aqueous sodium hydroxide, then were extracted with chloroform (4×). The organic layers were combined, washed with saturated aqueous sodium bicarbonate (5 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield a foam. The foam was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 3-35% CMA in chloroform) followed by crystallization from acetonitrile. The crystals were isolated by filtration and dried under vacuum at 70° C. to yield 80 mg of N-[4-(4-amino-2-{[(isopropylamino)oxy]methyl}-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]benzamide as a white powder, mp 161.0-162.0° C.

Provenance & Evidence