Trifluoroacetic acid → (2R)-4-(5-(Isoquinolin-6-yl)-1,3,4-oxadiazol-2-yl)-1-(4-(trifluoromethyl)phenyl)butan-2-amine

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Reaction Steps

tert-Butyl(R)-4-(5-(isoquinolin-6-yl)-1,3,4-oxadiazol-2-yl)-1-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate (0.060 g, 0.12 mmol) was stirred with 10 mL TFA in 10 mL DCM for 1 hour. After removing the solvent, the remaining residue was made basic with 2 M ammonia in MeOH and purified by chromatography on silica gel (4% 2M ammonia MeOH solution in DCM) to give the desired product as a white solid (0.045 g, 93%). LCMS (API-ES) m/z: 413 (M+H+); 1H NMR (400 MHz, CD3OD) δ ppm 1.87-1.97 (m, 1H), 2.17-2.27 (m, 1H), 2.63-2.79 (m, 2H), 2.91-2.98 (m, 1H), 3.12 (dd, J=13.40, 5.18 Hz, 1H), 4.18-4.25 (m, 1H), 7.50 (d, J=8.02 Hz, 2H), 7.64 (d, J=8.02 Hz, 2H), 7.92 (d, J=5.67 Hz, 1H), 8.14-8.19 (m, 1H), 8.22-8.27 (m, 1H), 8.50 (d, J=5.48 Hz, 1H), 9.30 (s, 1H), one H was obscured.

Provenance & Evidence