反应 #45853

反应方程式

dimethyl sulfoxide

(3S)-3-(dimethylamino)pyrrolidine

dimethyl sulfoxide

4-cyano-N-ethyl-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

triethylamine

→

compound

收率 52.2%

4-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-N-ethyl-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

收率 52.2%

溶剂

brine

反应条件

后处理

1. 1
   温度After cooling
2. 2
   其他the reaction liquid
3. 3
   萃取was extracted with ethyl acetate
4. 4
   洗涤Next, the combined organic layer was washed with saturated brine
5. 5
   干燥dried over anhydrous magnesium sulfate
6. 6
   过滤filtered
7. 7
   浓缩the filtrate was concentrated under the reduced pressure
8. 8
   其他The resulting residue was purified by preparative TLC (eluent, dichloromethane

实验过程

Under nitrogen atmosphere, a dimethyl sulfoxide (1 ml) solution of (3S)-3-(dimethylamino)pyrrolidine (80 μl, 633 μmol) was added at 140 to 150° C. to a dimethyl sulfoxide (10 ml) solution of 4-cyano-N-ethyl-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-285) (178 mg, 528 μmol) and triethylamine (96 μl, 686 μmol), followed by stirring at the same temperature for 165 minutes. After cooling, saturated brine was added to the reaction liquid, and the reaction liquid was extracted with ethyl acetate. Next, the combined organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under the reduced pressure. The resulting residue was purified by preparative TLC (eluent, dichloromethane:methanol=10:1, v/v) to obtain the entitled compound (119 mg, 52%) as an amorphous substance.

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