반응 #45893

반응 방정식

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

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

→

compound

수율 64.0%

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

수율 64.0%

용매

dimethyl sulfide

반응 조건

후처리

1. 1
   온도After cooled
2. 2
   농축this was concentrated under reduced pressure
3. 3
   workup.ADDITIONdiluted with chloroform
4. 4
   세척washed with saturated brine
5. 5
   건조The organic layer was dried over anhydrous magnesium sulfate
6. 6
   기타the solvent was evaporated away under reduced pressure
7. 7
   기타The resulting residue was purified by preparative TLC (eluent, chloroform

실험 절차

6-Dimethylamino-2-Cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-321) (34 mg, 0.10 mmol) was dissolved in dimethyl sulfide (4 ml), then triethylamine (29 μl, 0.20 mmol) and (3S)-3-(dimethylamino)pyrrolidine (27 μl, 0.21 mmol) were added, followed by stirring under nitrogen atmosphere at 100° C. for 24 hours. After cooled, this was concentrated under reduced pressure, diluted with chloroform, and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure. The resulting residue was purified by preparative TLC (eluent, chloroform:methanol=10:1, v/v) to obtain the entitled compound (20 mg, 64%) as a white crystal.

출처