반응 #45856

반응 방정식

sodium hydrogencarbonate

triethylamine

(3S)-3-(methylamino)pyrrolidine

2-Cyclopropyl-7-fluoro-5-methyl-6-phenylbenzoxazole-4-carbonitrile

→

compound

수율 63.0%

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

수율 63.0%

용매

ethyl acetate

dimethyl sulfoxide

반응 조건

후처리

1. 1
   온도this was cooled to room temperature
2. 2
   기타The reaction liquid
3. 3
   추출The aqueous layer was further extracted twice with ethyl acetate
4. 4
   세척washed with saturated brine
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   기타The insoluble matter was separated by filtration
7. 7
   기타the solvent was evaporated away
8. 8
   기타the resulting residue was purified by preparative TLC (eluent, chloroform

실험 절차

2-Cyclopropyl-7-fluoro-5-methyl-6-phenylbenzoxazole-4-carbonitrile (I-173) (250 mg, 0.86 mmol) was dissolved in dimethyl sulfoxide (5 ml), then at room temperature, triethylamine (155 μl, 1.11 mmol) and (3S)-3-(methylamino)pyrrolidine (119 μl, 1.11 mmol) were added. After stirred under nitrogen atmosphere at 90° C. for 13 hours, this was cooled 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=93:7, v/v) to obtain the entitled compound (201 mg, 63%) as a white solid.

출처