Tetrahydrofuran → N-(5-Amino-2-(morpholine-4-carbonyl)phenyl)-N-methylmethanesulfonamide

Participants

Reaction Steps

A suspension of N-methyl-N-(2-(morpholine-4-carbonyl)-5-nitrophenyl)methanesulfonamide (101.3 mg, 0.295 mmol), zinc (193 mg, 2.95 mmol), ammonium chloride (158 mg, 2.95 mmol) in MeOH (0.5 mL), and THF (0.5 mL) was stirred at room temperature for 16 h. The crude material was loaded onto a silica gel cartridge and dried in vacuo. The dry cartridge was then connected to an ISCO cartridge, eluting with 2-10% MeOH in CH2Cl2 to give the desired product as white solid (68.2 mg, 74% yield). LCMS: (M+H)+=314.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.94 (1H, d, J=8.28 Hz), 6.61 (1H, br. s.), 6.53 (1H, dd, J=8.28, 2.01 Hz), 5.52 (2H, s), 3.51 (4H, br. s.), 3.19-3.26 (1H, m), 3.15-3.18 (3H, m), 3.08 (3H, br. s.), 3.03 (3H, br. s.).

Provenance & Evidence