Acetyl chloride → 1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

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Reaction Steps

Under a nitrogen atmosphere, a solution of acetyl chloride (15 mmol) in anhydrous ethanol (50 mL) was stirred for 15 minutes and then added to 5-(2-aminophenyl)-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrile (2.75 g). The reaction was heated at reflux under nitrogen for 16 hours, allowed to cool to room temperature, and concentrated under reduced pressure. The residue was partitioned between 2M aqueous sodium carbonate and chloroform. The aqueous layer was separated and extracted twice with chloroform. The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product (2.81 g) was purified by automated flash chromatography (eluting with 0% to 20% CMA in chloroform) and then recrystallized from acetonitrile (50 mL). The crystals were dried overnight at 33 Pa and 98° C. to provide 1.65 g of 1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine as white needles, mp 191-192° C.

Provenance & Evidence