4-Toluenesulfonyl chloride → HCID 57447128, compound

Participants

Reaction Steps

mCPBA (953 mg of 77% pure material, 4.25 mmol) was added to a solution of 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexanecarboxamide (1.30 g, 3.54 mmol) in chloroform (15 mL); the reaction was stirred for one hour at ambient temperature. Ammonium hydroxide (15 mL) and p-toluenesulfonyl chloride (742 mg, 3.89 mmol) were added, and the mixture was stirred vigorously for two hours. The aqueous fraction was separated and extracted several times with chloroform. The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (eluting with 2-7% methanol in dichloromethane) followed by recrystallization from acetonitrile to provide 1-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexanecarboxamide as a tan crystalline solid, mp 221-223° C.

Provenance & Evidence