Benzenesulfonyl chloride → HCID 58869108, compound

Participants

Reaction Conditions

Reaction Steps

3-Chloroperoxybenzoic acid (77% pure, 0.44 g, 1.95 mmol) (mCPBA) was added to a solution of N-methoxy-N-[4(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]acetamide (1.0 mmol) in dichloromethane (25 mL) cooled to 0° C. and stirred for 10 minutes, and then the reaction was stirred for one hour at ambient temperature. Concentrated ammonium hydroxide (10 mL) and phenylsulfonyl chloride (0.22 mL, 1.75 mmol) were sequentially added and the reaction mixture was stirred for 1 hour and then diluted with dichloromethane (50 mL) and saturated aqueous sodium bicarbonate solution (2×50 mL) containing 5% sodium hydroxide (5 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (2×25 mL) and the combined organic solutions were dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide a brown oil. The material was purified by flash column chromatography on silica gel (eluting with 5% methanol and concentrated ammonium hydroxide (2 mL) in dichloromethane). The resulting crystalline solid was recrystallized twice from acetonitrile and water and dried overnight under vacuum at 70° C. to afford 0.26 g of N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N-methoxyacetamide as light yellow needles, mp 138-140° C. MS (APCI) m/z 370 (M+H+); Anal. calcd for C20H27N5O2: C, 65.02; H, 7.37; N, 18.96. Found: C, 64.97; H, 7.04; N, 18.80.

Provenance & Evidence