(S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-(4-fluorobenzylidene)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → (2S,4S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-(4-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Participants

Reaction Steps

Step (c) A flask was charged with (S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-(4-fluorobenzylidene)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (15 mg, 0.027 mmol), palladium on carbon (10%, 50 mg) and methanol (5 mL) and the mixture was placed under a hydrogen atmosphere (balloon). The mixture was stirred for 2 hours at ambient temperature and then concentrated. Product was purified from the residue by chromatography (EtOAc to EtOAc/MeOH (9:1)+1% NEt3) to give Compound 76, (2S,4S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-(4-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (10 mg, 0.019 mmol, 69%), as an off-white solid. 1H-NMR (400 MHz, CDCl3): 8.61 (s, 1H), 8.22 (s, 1H), 7.98 (s, 1H), 7.45 (d, J=10.0 Hz, 2H), 7.18-7.14 (m, 2H), 7.03-6.91 (m, 8H), 5.00 (m, 2H), 4.62 (m, 1H), 3.76 (dd, J=11.2, 7.6 Hz, 1H), 3.25 (m, 1H), 2.85 (dd, J=12.8, 7.6 Hz, 1H), 2.73 (dd, J=12.8, 7.6 Hz, 1H), 2.57 (m, 1H), 2.30 (m, 2H). MS (EI) for C28H25F2N5O3. found 518.2 (MH+).

Provenance & Evidence