تفاعل #45725

معادلة التفاعل

ethyl acetate

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

2-Cyclopropyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

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product

المردود 69.0%

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

المردود 69.0%

المذيبات

brine

dimethyl sulfoxide

ظروف التفاعل

المعالجة

1. 1
   أخرىthe reaction liquid
2. 2
   استخلاصThe aqueous layer was further extracted twice with ethyl acetate
3. 3
   غسيلwashed with saturated brine
4. 4
   تجفيفdried over anhydrous sodium sulfate
5. 5
   أخرىThe insoluble matter was separated by filtration
6. 6
   أخرىthe solvent was evaporated away
7. 7
   أخرىthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=97:3)

الإجراء التجريبي

2-Cyclopropyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-173) (70 mg, 0.24 mmol) was dissolved in dimethyl sulfoxide (2 ml), then at room temperature, triethylamine (50 μl, 0.36 mmol) and (3S)-3-(dimethylamino)pyrrolidine (40 μl, 0.31 mmol) were added. After cooling to room temperature, the reaction liquid was fractionated with ethyl acetate and saturated brine. The aqueous layer was further 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, then the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=97:3) to obtain a roughly-purified product (64 mg, 69%).

المصدر