Benzenesulfonyl chloride → 2-(2-methoxyethyl)-1-(5-morpholin-4-yl-5-oxopentyl)-1H-imidazo[4,5-c]quinolin-4-amine

Participants

Reaction Steps

mCPBA (6.60 g, 28.7 mmol) was added to a solution of 2-(2-methoxyethyl)-1-(5-morpholin-4-yl-5-oxopentyl)-1H-imidazo[4,5-c]quinoline (6.5 g, 17 mmol) in chloroform (100 mL); the reaction was stirred for two hours at ambient temperature. The reaction was cooled to 0° C., and ammonium hydroxide (50 mL) was added. A solution of benzenesulfonyl chloride (4.11 mL, 33.0 mmol) in chloroform (20 mL) was added over a period of 20 minutes, and the reaction was allowed to warm to ambient temperature and stirred for two hours. The work-up procedure and chromatographic purification was carried out as described in Part D of Example 8. The resulting product was triturated with 10% aqueous sodium hydroxide, isolated by filtration, washed with water, and dried overnight in a vacuum oven to provide 2-(2-methoxyethyl)-1-(5-morpholin-4-yl-5-oxopentyl)-1H-imidazo[4,5-c]quinolin-4-amine as an off-white powder, mp 128-129° C.

Provenance & Evidence