Diisopropylethylamine → 3-Fluoro-5-(morpholin-4-yl)-N-[2-(tritylsulfanyl)benzyl]benzamide

Participants

Reaction Steps

A suspension of 1-[2-(tritylsulfanyl)phenyl]methanamine (335 mg, 0.88 mmol), 3-fluoro-5-morpholin-4-yl-benzoic acid (WO2004/089929) (237 mg, 1.05 mmol) and DIPEA (0.38 mL, 2.19 mmol) in DMF (15 mL) was treated with HATU (400 mg, 1.05 mmol). The mixture was stirred at RT for 45 min, then partitioned between aqueous saturated NaHCO3 and EtOAc. The organic layer was separated, dried over MgSO4, filtered, and the filtrate was concentrated in vacuo to afford the title compound (quantitative) as an off-white solid. 1H NMR (300 MHz, CDCl3): δ 7.35-7.29 (6H, m), 7.27-7.19 (10H, m), 7.17 (2H, m), 7.10 (1H, t, J 1.7), 6.98-6.92 (1H, m), 6.73-6.64 (2H, m), 5.98 (1H, br t, J 6), 4.21 (2H, d, J 6), 3.84 (4H, t, J 4.8), 3.19 (4H, t, J 4.8).

Provenance & Evidence