反应 #45682

反应方程式

ethyl acetate

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

2-(Diethylamino)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

→

compound

收率 65.9%

2-(Diethylamino)-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

收率 65.9%

溶剂

brine

dimethyl sulfoxide

反应条件

后处理

1. 1
   温度After cooling to room temperature
2. 2
   其他the reaction liquid
3. 3
   其他The aqueous layer was separated
4. 4
   萃取this was extracted twice with ethyl acetate
5. 5
   洗涤washed with saturated brine
6. 6
   干燥dried over anhydrous sodium sulfate
7. 7
   其他The insoluble matter was separated by filtration
8. 8
   其他the solvent was evaporated away
9. 9
   其他the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=92:8)

实验过程

2-(Diethylamino)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-133) (78 mg, 0.24 mmol) was dissolved in dimethyl sulfoxide (2 ml) in a sealed tube, then triethylamine (67 μl, 0.48 mmol) and (3S)-3-(dimethylamino)pyrrolidine (61 μl, 0.48 mmol) were added. The reaction system was heated at 150° C. for 4.5 hours and then at 100° C. for 60 hours. After cooling to room temperature, the reaction liquid was fractionated with ethyl acetate and saturated brine. The aqueous layer was separated, and this was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=92:8) to obtain the entitled compound (66 mg, 65%) as a brown solid.

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