Hydrochloric Acid → 2-amino-1-(2-(3-aminopropyl)-5-(2,5difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)propan-1-one

Participants

Reaction Steps

2-Amino-1-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)propan-1-one (50 mg, 0.116 mmol) was dissolved in 5.0 mL of MeOH. HCl (0.46 ml, 0.464 mmol) was added followed by evacuation/re-vacuation with N2. Pd/C (12 mg, 0.011 mmol) was then added followed by H2 balloon. Following 40 hours at 23° C., the reaction was concentrated in vacuo, affording the product (41 mg, 87%) as a cream/yellow colored foam. MS ESI (+) m/z 405 (M+1) detected; 1H NMR (400 MHz, CD3OD) δ7.68 (m, 1H), 7.53 (m, 2H), 7.42 (t, 2H, J=9 Hz), 7.34 (m, 3H), 4.92 (m, 1H), 3.22 (m, 2H), 3.17 (m, 4H), 2.65 (m, 2H), 2.20 (m, 1H), 1.99 (m, 1H), 1.72 (d, 1.5 H, J=8 Hz), 1.66 d, 1.5 H, J=8 Hz).

Provenance & Evidence