Trifluoroacetic acid → 3-(5-Phenyl-1,3,4-oxadiazol-2-yl)-5-(piperazin-1-yl)pyrazin-2-amine

HRID 1959364노트

반응식

HRID 1959364 반응식
[C:1]1([C:7]2[O:11][C:10]([C:12]3[C:13]([NH:24]C(=O)OC(C)(C)C)=[N:14][CH:15]=[C:16]([N:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)[N:17]=3)=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]1([C:7]2[O:11][C:10]([C:12]3[C:13]([NH2:24])=[N:14][CH:15]=[C:16]([N:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)[N:17]=3)=[N:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 66745759Tert-butyl 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-5-(piperazin-1-yl)pyrazin-2-ylcarbamate

생성물 1

HCID 667444203-(5-Phenyl-1,3,4-oxadiazol-2-yl)-5-(piperazin-1-yl)pyrazin-2-amine수율 82.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Tert-butyl 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-5-(piperazin-1-yl)pyrazin-2-ylcarbamate (2.29 g, 5.408 mmol) was dissolved in DCM (20 mL) and treated with TFA (5 mL, 64.90 mmol) was added. The reaction was allowed to stir for 1 hour at ambient temperature and then the solvent removed in vacuo. The mixture was treated with NaHCO3/brine and EtOAc and the 2 layers separated layers. The aqueous layer was extracted with EtOAc, followed by DCM and CHCl3. The mixture was dried over MgSO4, filtered and concentrated to give the product as an orange solid (1.44 g, 82% Yield). 1H NMR (400.0 MHz, DMSO) d 3.00 (4H, br m), 3.43 (4H, br m), 6.05 (2H, br s), 7.20 (1H, m), 7.34 (2H, m), 7.90 (1H, m), 8.13 (2H, m) ppm; (ES+) 324.03

후처리

  1. additionwas added
  2. customthe solvent removed in vacuo
  3. additionThe mixture was treated with NaHCO3/brine and EtOAc
  4. customthe 2 layers separated layers
  5. extractionThe aqueous layer was extracted with EtOAc
  6. dry with materialThe mixture was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-afa7db4208c54b09bd04c7118d7a3a2c
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410112B2

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