Ammonia → HCID 66814387, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-(2-amino-4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)butylcarbamate (5.5 g, 14 mmol) and ammonia (50 mL of a 7 N solution in methanol) were added to a high-pressure vessel, which was sealed and heated in an oven at 170° C. for two days. The resulting solution was allowed to cool to room temperature and concentrated under reduced pressure. The resulting dark oil was partially dissolved in methanol, and diethyl ether was added. The mixture was stirred for one hour, and a solid was isolated by filtration. The solid was washed sequentially with diethyl ether and 90:10 dichloromethane:methanol (100 mL) and dried on the filter funnel for 30 minutes. The resulting green solid (2.52 g) was purified by automated flash chromatography on silica gel (eluting with aqueous ammonium hydroxide:methanol:dichloromethane in a gradient from 0:0:100 to 2.5:47.5:50) to provide 167 mg of 1-(4-aminobutyl)-1H-imidazo[4,5-c]quinoline-2,4-diamine as a dark green solid.

Provenance & Evidence