Ammonia → HCID 59026683, compound

Participants

Reaction Steps

A slurry of 4-chloro-2-(ethoxymethyl)-1-[3-(3-pyridin-3-ylisoxazol-5-yl)propyl]-1H-imidazo[4,5-c]quinoline (1.78 g, 3.97 mmol) in a solution of 7 M ammonia in methanol (20 mL) was heated at 150° C. for 20 hours in a Parr pressure vessel. The volatiles were removed under reduced pressure and the resulting oil was partitioned between dichloromethane and 1 M KOH. The aqueous layer was extracted with dichloromethane. The organic layers were combined, washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography (silica gel, gradient elution from 9:1 to 4:1 chloroform/CMA). After concentration of the appropriate fractions, a white solid was obtained. The white solid was triturated with diethyl ether and dried at 80° C. under vacuum to provide 2-(ethoxymethyl)-1-[3-(3-pyridin-3-ylisoxazol-5-yl)propyl]-1H-imidazo[4,5-c]quinolin-4-amine as a white powder, mp 199.0-200.0° C.

Provenance & Evidence