反应详情

N-[2-(7-Benzyloxy-2-ethoxymethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]acetamide (1.77 g, 3.83 mmol) was dissolved in dichloromethane (100 mL) and aqueous ammonium hydroxide (10 mL) was added, followed by para-toluenesulfonyl chloride (0.73 g, 3.83 mmol). After stirring for 5 hours, the organic and aqueous phases were separated and the organic fraction was washed twice with saturated sodium bicarbonate and then once with brine. The organic fraction was then dried over sodium sulfate, filtered, and concentrated to give a dark orange solid. The solid was purified by flash column chromatography on silica gel (eluting with a gradient of 6-7.5% methanol in dichloromethane) followed by recrystallization from acetonitrile to provide 1.27 g of N-[2-(4-amino-7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]acetamide as a white powder, mp 202.0-205.0° C.

1. customthe organic and aqueous phases were separated
2. washthe organic fraction was washed twice with saturated sodium bicarbonate
3. dry with materialThe organic fraction was then dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customto give a dark orange solid
7. customThe solid was purified by flash column chromatography on silica gel (
8. washeluting with a gradient of 6-7.5% methanol in dichloromethane)
9. customfollowed by recrystallization from acetonitrile