Ethyl Acetate → HCID 66814331, compound

Participants

Reaction Conditions

Reaction Steps

Cyanogen bromide (1.11 g, 10.5 mmol) was added to a solution of 5,6-dimethyl-N4-(2-methylpropyl)-2-phenoxypyridine-3,4-diamine (2.5 g, 8.8 mmol) in ethanol (50 mL), and the solution was heated overnight at 90° C. An analysis by LC/MS indicated the presence of starting material, and additional cyanogen bromide (100 mg) was added. The reaction was heated for one additional hour and allowed to cool to ambient temperature. Ethyl acetate and saturated aqueous sodium bicarbonate were added. The organic layer was separated, washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with 2-5% methanol in dichloromethane) to provide 1.46 g of 6,7-dimethyl-1-(2-methylpropyl)-4-phenoxy-1H-imidazo[4,5-c]pyridin-2-amine hydrobromide as a white powder.

Provenance & Evidence