반응 #45730
ord-10b35e463ed443d2b0cd50bb67c59fcc
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후처리
- 1온도After cooling to room temperature
- 2기타the reaction liquid
- 3추출The aqueous layer was further extracted twice with ethyl acetate
- 4세척washed with saturated brine
- 5건조dried over anhydrous sodium sulfate
- 6기타The insoluble matter was separated by filtration
- 7기타the solvent was evaporated away
- 8기타the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=96:4)
- 9기타to obtain a roughly-purified product (211 mg, 74% for 2 steps) as a white solid
- 10기타This was recrystallized from ethyl acetate and diisopropyl ether
실험 절차
2-Cyclopropyl-6-(3,5-difluorophenyl)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-176) (including impurities, estimated as 0.68 mmol) was dissolved in dimethyl sulfoxide (5 ml), then at room temperature, triethylamine (142 μl, 1.02 mmol) and (3S)-3-(dimethylamino)pyrrolidine (112 μl, 0.88 mmol) were added, the solution was stirred under nitrogen atmosphere at 90° C. for 15 hours. After cooling to room temperature, the reaction liquid was fractionated with ethyl acetate and an aqueous saturated sodium hydrogencarbonate solution. 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=96:4) to obtain a roughly-purified product (211 mg, 74% for 2 steps) as a white solid. This was recrystallized from ethyl acetate and diisopropyl ether to obtain the entitled compound (46 mg) as a white solid.