4-Toluenesulfonyl chloride → HCID 57447022, compound

Participants

Reaction Steps

mCPBA (5.0 g, 29.03 mmol) was added to a solution of N-methyl-6-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanamide (3.42 g, 9.67 mmol) in chloroform (100 mL). The reaction was stirred for two hours at ambient temperature and then washed with 10% aqueous sodium hydroxide. Ammonium hydroxide (40 mL) and p-toluenesulfonyl chloride (2.39 g, 12.6 mmol) were sequentially added, and the reaction was stirred vigorously for two hours. The organic layer was separated and washed sequentially with 10% sodium hydroxide, saturated aqueous sodium bicarbonate, and brine; dried over magnesium sulfate; filtered; and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol) followed by recrystallization from methanol:water to provide 1.055 g of 6-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-N-methylhexanamide as beige needles, mp 158-159° C.

Provenance & Evidence