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

Participants

Reaction Steps

mCPBA (6.56 g, 28.5 mmol) was added to a solution of 1-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-1H-imidazo[4,5-c]quinoline (6.2 g, 16 mmol) in chloroform (100 mL); the reaction was stirred for three hours at ambient temperature. Ammonium hydroxide (50 mL) was added. p-Toluenesulfonyl chloride (6.056 g, 31.76 mmol) was added over a period of five minutes, and the reaction was stirred for one hour. The work-up procedure and chromatographic purification was carried out as described in Part D of Example 8. The resulting oil was triturated with acetone, isolated by filtration, and dried to provide 1-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine as a tan powder, mp 178-179° C.

Provenance & Evidence