反应详情

Ethoxyacetyl chloride (6.2 g, 50.5 mmol) was added dropwise to a solution of crude 1-[(3-amino-6-bromoquinolin-4-yl)amino]-2-methylpropan-2-ol, dichloromethane (500 mL), and triethylamine (7 mL, 50.5 mmol). After stirring for 16 hours, water was added and the mixture was stirred for an additional 2 hours. The fractions were separated. The organic fraction was washed with water, concentrated under reduced pressure and redissolved in ethanol (500 mL). Water (150 mL) and potassium carbonate (10.5 g) were added and the mixture was heated at reflux temperature for 3 hours. The ethanol was removed under reduced pressure. The remaining aqueous fraction was extracted with ethyl acetate (2×500 mL). The organic fractions were combined, washed with water followed by saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. Recrystallization from acetonitrile provided 10.4 g of 1-[8-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as a tan powder.

1. stirringthe mixture was stirred for an additional 2 hours
2. customThe fractions were separated
3. washThe organic fraction was washed with water
4. concentrationconcentrated under reduced pressure
5. dissolutionredissolved in ethanol (500 mL)
6. additionWater (150 mL) and potassium carbonate (10.5 g) were added
7. temperaturethe mixture was heated
8. temperatureat reflux temperature for 3 hours
9. customThe ethanol was removed under reduced pressure
10. extractionThe remaining aqueous fraction was extracted with ethyl acetate (2×500 mL)
11. washwashed with water
12. dry with materialdried over anhydrous sodium sulfate
13. filtrationfiltered
14. concentrationconcentrated under reduced pressure
15. customRecrystallization from acetonitrile