4-Toluenesulfonyl chloride → 1-[3-(aminooxy)propyl]-7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[3-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propoxy]-1H-isoindole-1,3(2H)-dione (1.00 g, 2.03 mmol) in chloroform (20 mL) at room temperature and under an atmosphere of nitrogen was added mCPBA (1.00 g, 4.06 mmol). The reaction was stirred for 2 hours, then was cooled to 0° C. Concentrated ammonium hydroxide (1 mL) was added followed by p-toluenesulfonyl chloride (111 mg, 0.58 mmol) in portions. The mixture was stirred for 1.5 hours at 0° C. and then filtered to remove a solid, which was washed with chloroform. The filtrate was washed with brine (2×10 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-35% CMA in chloroform) to afford 300 mg of 1-[3-(aminooxy)propyl]-7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine.

Provenance & Evidence