反应详情

温度

150 °C

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.

1. customThe volatiles were removed under reduced pressure
2. customthe resulting solid was triturated with 1 M aqueous sodium hydroxide
3. customisolated by filtration
4. customThe crude product was purified by flash chromatography (silica gel, gradient elution from 10% to 20% CMA in chloroform)
5. concentrationconcentrated
6. customto yield a solid
7. customthat was triturated with hot diethyl ether and 9:1 dichloromethane/methanol (10 mL)
8. dry with materialThe final material was dried at 80° C. under vacuum