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

HRID 1959364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1959364
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 667444203-(5-Phenyl-1,3,4-oxadiazol-2-yl)-5-(piperazin-1-yl)pyrazin-2-amineAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-afa7db4208c54b09bd04c7118d7a3a2c
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410112B2

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