Trifluoroacetic acid → (S)-1-(6-Fluoro-1-isopropyl-1H-benzoimidazol-2-yl)ethylamine
Reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([CH:15]([CH3:17])[CH3:16])[C:13]2[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:22][C:19]1[CH:20]=[CH:21][C:12]2[N:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[N:14]([CH:15]([CH3:17])[CH3:16])[C:13]=2[CH:18]=1Participants
4
Procedure
[(S)-1-(6-Fluoro-1-isopropyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester (1.0 g, 3.11 mmol) was dissolved in DCM (10 mL) and TFA (5 mL) added. The reaction mixture was stirred at RT for 30 minutes. The resultant mixture was concentrated in vacuo and the residue dissolved in DCM (40 mL) and stirred vigorously with saturated aqueous NaHCO3 (20 mL), for 10 minutes. The layers were separated and the organic fraction washed with brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo to afford the title compound (0.5 g, 72%). 1H NMR (CDCl3, 400 MHz): δ 7.65 (1H, dd, J=8.83, 5.01 Hz), 7.20 (1H, dd, J=9.40, 2.46 Hz), 6.97 (1H, ddd, J=9.58, 8.80, 2.43 Hz), 4.92-4.82 (1H, m), 4.37-4.28 (1H, q, J=6.68 Hz), 1.64 (6H, d, J=6.98 Hz), 1.58 (3H, d, J=6.65 Hz).