Ammonia → 2-(ethoxymethyl)-1-[3-(3-phenylisoxazol-5-yl)propyl]-1H-imidazo[4,5-c]quinolin-4-amine

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Reaction Conditions

Reaction Steps

A mixture of 4-chloro-2-(ethoxymethyl)-1-[3-(3-phenylisoxazol-5-yl)propyl]-1H-imidazo[4,5-c]quinoline (2.22 g, 4.97 mmol) in a solution of 7 M ammonia in methanol (25 mL) was heated at 150° C. for 17 hours in a Parr pressure vessel. The volatiles were removed under reduced pressure and the resulting solid was triturated with 1 M aqueous sodium hydroxide and isolated by filtration. The crude product was purified by flash chromatography (silica gel, gradient elution from 10% to 20% CMA in chloroform). The appropriate fractions were combined and concentrated to yield a solid that was triturated with hot diethyl ether and 9:1 dichloromethane/methanol (10 mL). The final material was dried at 80° C. under vacuum to yield 2-(ethoxymethyl)-1-[3-(3-phenylisoxazol-5-yl)propyl]-1H-imidazo[4,5-c]quinolin-4-amine (954 mg) as a white powder, mp 171.0-172.0° C.

Provenance & Evidence