Step (b) Benzyl bromide (0.131 mL, 1.10 mmol) was added to a flask charged with (2S,4S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-amino-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (0.465 g, 1.10 mmol), DMF (10 mL), and K2CO3 (0.607 g, 4.40 mmol). The reaction mixture was stirred at ambient temperature for 30 minutes and then diluted with 1N hydrochloric acid (30 mL). The dilution was washed with ethyl acetate (30 mL). The aqueous layer was basified with 2N sodium hydroxide (40 mL) and then extracted with methylene chloride (40 mL). The extract was washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated. Product was purified from the residue by reverse phase HPLC to give Compound 80, (2S,4S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-(benzylamino)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (126 mg, 0.245 mmol, 22%), as an off-white solid. 1H-NMR (400 MHz, CDCl3): 12.08 (br. s, 1H), 11.13 (s, 1H), 9.05 (s, 1H), 8.24-8.16 (m, 1H), 7.99-7.94 (m, 1H), 7.41-7.20 (m, 4H), 7.04-6.82 (m, 7H), 5.21 (d, J=16.0 Hz, 1H), 5.00 (s, 1H), 4.93 (d, J=16.0 Hz, 1H), 4.74-4.57 (m, 1H), 3.96-5.59 (m, 3H), 3.14-3.07 (m, 2H), 2.62-2.00 (m, 2H). MS (EI) for C28H27FN6O3. found 515.2 (MH+).
