Ammonia → N-[2-(2,4-diamino-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide

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Reaction Conditions

Reaction Steps

Crude N-[2-(2-amino-4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide hydrobromide (0.400 g) and ammonia (25 mL of a 7 N solution in methanol) were added to a high-pressure vessel, which was sealed and heated overnight in an oven at 150° C. The resulting solution was concentrated under reduced pressure, and the residue was purified by flash chromatography on silica gel (eluting with 2-6% methanol in dichloromethane with 1% ammonium hydroxide added.) A portion of the product was recrystallized from acetonitrile and a small amount of methanol, isolated by filtration, and washed with diethyl ether to provide 39 mg of N-[2-(2,4-diamino-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide as brown needles, mp >230° C.

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