Trifluoroacetic acid → (S)-N1-(5-(isoquinolin-6-yl)-1,3,4-oxadiazol-2-yl)-3-(4-(trifluoromethyl)phenyl)propane-1,2-diamine

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Reaction Steps

tert-Butyl(S)-1-(5-(isoquinolin-6-yl)-1,3,4-oxadiazol-2-ylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (0.04 g, 0.078 mmol) was treated with 2 mL TFA in 2 mL DCM for 30 minutes. After removing the solvent, the remaining residue was made basic with 2M ammonia in MeOH and loaded on a preparative TLC plate. The TLC plate was developed with 5% 2M ammonia in MeOH in DCM. A white solid was obtained as the desired product (20 mg, 63%). LCMS (API-ES) m/z (%): 414.0 (100%, M++H); 1H NMR (400 MHz, CD3OD) δ ppm 2.72 (dd, J=13.60, 7.53 Hz, 1H) 2.94 (dd, J=13.50, 5.28 Hz, 1H) 3.30-3.37 (m, 2H) 3.39-3.45 (m, 1H) 7.43 (d, J=8.02 Hz, 2H) 7.56 (d, J=8.22 Hz, 2H) 7.87 (d, J=5.87 Hz, 1H) 8.10-8.15 (m, 1H) 8.16-8.20 (m, 1H) 8.34 (s, 1H) 8.47 (d, J=5.87 Hz, 1H) 9.24 (s, 1H).

Provenance & Evidence