반응 #45631

반응 방정식

ethyl acetate

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

2-(4-Cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)-2-methylpropanamide

→

compound

수율 55.0%

2-{4-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}-2-methylpropanamide

수율 55.0%

용매

water

dimethyl sulfoxide

반응 조건

후처리

1. 1
   온도After cooling to room temperature
2. 2
   세척The organic layer was washed with saturated brine
3. 3
   건조dried over anhydrous sodium sulfate
4. 4
   기타The solvent was evaporated away
5. 5
   세척eluted with a mixed solvent of chloroform/methanol (10:1

실험 절차

2-(4-Cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)-2-methylpropanamide (I-96) (58 mg, 0.17 mmol) was dissolved in dimethyl sulfoxide (1.2 ml), triethylamine (33 μl, 0.24 mmol) and (3S)-3-(dimethylamino)pyrrolidine (26 μl, 0.21 mmol) were added, followed by stirring at 90° C. for 3 hours under nitrogen atmosphere. After cooling to room temperature, ethyl acetate was added, followed by fractionation with water. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated away and the resulting residue was subjected to preparative silica gel column chromatography, eluted with a mixed solvent of chloroform/methanol (10:1, v/v) to obtain the entitled compound (41 mg, 0.09 mmol, 55%) as a white solid.

출처