2-(ethoxymethyl)-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N,N-bis(4-methoxybenzyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine → HCID 59026705, compound

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Reaction Steps

A solution of 2-(ethoxymethyl)-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N,N-bis(4-methoxybenzyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (3.55 g, 5.58 mmol) in trifluoroacetic acid (30 mL) was stirred at room temperature for three days. The trifluoroacetic acid was removed under reduced pressure, and the residue was triturated with hydrochloric acid (50 mL of a 6 N in ethanol) and water (10 mL) for 30 minutes. The resulting mixture was adjusted to pH 14 with the addition of 50% (w/w) aqueous sodium hydroxide and stirred for 30 minutes. The volatiles were removed under reduced pressure, and the residue was recrystallized from aceotnitrile after a hot filtration. Three crops of crystals were collected to provide 1.35 g of 2-(ethoxymethyl)-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine. A portion of this material was diluted with dichloromethane. The resulting solution was washed sequentially with aqueous potassium carbonate, water, and brine; purified by column chromatography on silica gel (250 g, eluting with 15% CMA in chloroform); and dried to provide 0.657 g of an analytically pure sample as a white powder, mp 246.0-247.0° C.

Provenance & Evidence