反应详情

温度

75 °C

A mixture of 4-amino-2-ethylthiazolo[4,5-c]quinolin-7-ol (245 mg, 1.0 mmol), cesium carbonate (1.3 g, 4.0 mmol), and DMF (20 mL) was stirred at 75° C. for 10 minutes. 2-(Bromomethyl)-5-(trifluoromethyl)furan (252 mg, 1.1 mmol) was added in portions over a period of 30 minutes. The reaction mixture was stirred for 1 hour and then the heat source was removed. The reaction mixture was diluted with water (250 mL), stirred for 1 hour, and then filtered. The isolated solid was rinsed with water and then dried to provide a brown powder. This material was dissolved in dichloromethane and then purified by HPFC eluting with a gradient of 0-15 CMA in chloroform 700 mL and then with 15% CMA in chloroform over 200 mL. The resulting solid was recrystallized from acetonitrile to provide 125 mg of 2-ethyl-7-{[5-(trifluoromethyl)furan-2-yl]methoxy}thiazolo[4,5-c]quinolin-4-amine as an off-white solid, mp 152-154° C. MS (ESI) m/z 394 (M+H)+; Anal. calcd for C18H14F3N3O2S: C, 54.96; H, 3.59; N, 10.68. Found: C, 54.90; H, 3.46; N, 10.52.

1. stirringThe reaction mixture was stirred for 1 hour
2. customthe heat source was removed
3. additionThe reaction mixture was diluted with water (250 mL)
4. stirringstirred for 1 hour
5. filtrationfiltered
6. washThe isolated solid was rinsed with water
7. customdried
8. customto provide a brown powder
9. custompurified by HPFC
10. washeluting with a gradient of 0-15 CMA in chloroform 700 mL
11. customThe resulting solid was recrystallized from acetonitrile