Trifluoroacetic acid → 3-(5-Phenyl-1,3,4-oxadiazol-2-yl)-5-(piperazin-1-yl)pyrazin-2-amine
Reaction equation
[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]=1Participants
4
Procedure
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