Ammonia → 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinolin-4-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinoline (0.2322 g, 0.6130 mmol) and 7 N ammonia in methanol (10 mL) was sealed in a pressure vessel and heated at 150° C. for 22 hours and allowed to cool to room temperature. The volatiles were removed under reduced pressure, and the resulting orange solid was triturated with diethyl ether. The solid was then purified by column chromatography on silica gel (7 g, eluting with 10% to 20% CMA in chloroform), triturated with diethyl ether, isolated by filtration, and dried. The solid was then boiled in methanol in the presence of a small amount of 0.5 N sodium hydroxide in methanol. The mixture was allowed to cool to room temperature, and the solid was isolated by filtration and dried to provide 0.0259 g of 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinolin-4-amine as a tan powder, mp 259.0-260.0° C.

Provenance & Evidence