4-Toluenesulfonyl chloride → HCID 57447016, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, a solution of 1-(6-morpholin-4-yl-6-oxohexyl)-2-propyl-1H-imidazo[4,5-c]quinoline (3.6 g, 9.1 mmol) in chloroform (100 mL) was treated with mCPBA (6.29 g, 36.5 mmol). The reaction was stirred for two hours, washed sequentially with saturated aqueous sodium bicarbonate (3×) and brine, dried over magnesium sulfate, and filtered. Concentrated ammonium hydroxide (40 mL) and p-toluenesulfonyl chloride (2.60 g, 13.7 mmol) were added sequentially to the filtrate. The reaction was stirred vigorously for two hours, and then the organic layer was separated and washed sequentially with 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 ethyl acetate:hexane to provide 0.84 g of 1-(6-morpholin-4-yl-6-oxohexyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine as brown needles, mp 149-151° C.

Provenance & Evidence