4-Toluenesulfonyl chloride → HCID 57447119, compound

Participants

Reaction Steps

mCPBA (1.68 g, 6.81 mmol) was added to a suspension of 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclopropanecarboxamide (1.70 g, 5.24 mmol) in chloroform (25 mL); the reaction was stirred for two hours at ambient temperature and then cooled to 0° C. Ammonium hydroxide (5 mL) and p-toluenesulfonyl chloride (1.10 g, 5.76 mmol) were added. The reaction was stirred for one hour at 5° C. and then filtered to isolate a precipitate. The precipitate was triturated with 2 M aqueous sodium hydroxide, isolated by filtration, triturated with hot acetonitrile, isolated by filtration, and recrystallized from ethanol. The crystals were dried overnight at 85° C. in a vacuum oven to provide 0.78 g of 1-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclopropanecarboxamide as tan needles, mp 230.5-232.5° C.

Provenance & Evidence