Reaction Steps
A mixture of fluoride 48 (103 mg, 0.22 mmol) and morpholine (2 mL) in DMSO (1 mL) was stirred in a sealed tube at 130° C. for 16 h. The solvent was evaporated and the residue was suspended in ice/water (50 mL) for 1 h. The precipitate was filtered, washed with water (5 mL) and dried. The crude solid was purified by column chromatography, eluting with a gradient (0-10%) of MeOH/EtOAc, to give benzamide 50 (83 mg, 71%) as a white powder: mp (EtOAc) 208-210° C.; 1H NMR δ 9.23 (s, 1H, CONH), 8.57 (br s, 1H, H-2′), 8.47 (br d, J=4.5 Hz, 1H, H-6′), 8.00 (br d, J=8.5 Hz, 2H, H-2, H-6), 7.91 (br d, J=8.5 Hz, 2H, H-3, H-5), 7.74 (br d, J=7.8 Hz, 1H, H-4′), 7.54 (d, J=9.0 Hz, 2H, H-3″, H-5″), 7.37 (dd, J=7.8, 4.7 Hz, 1H, H-5′), 7.05 (d, J=9.0 Hz, 2H, H-2″, H-6″), 4.49-4.54 (m, 4H, CH2SO2, CH2N), 3.72 (br t, J=4.8 Hz, 4H, 2×CH2O), 3.27 (br t, J=4.8 Hz, 4H, 2×CH2N), 2.13 (s, 3H, CH3); 13C NMR δ 165.5, 157.8, 154.2, 149.7, 148.8, 148.0, 135.3, 135.1, 134.8, 129.7 (2), 128.8, 128.0 (2), 126.4, 126.0, 125.4 (2), 123.4, 113.3 (2), 65.6 (2), 53.2, 46.7 (2), 40.4, 9.6; MS m/z 533.7 (MH+, 100%). Anal. calcd for C28H28N4O5S: C, 63.14; H, 5.30; N, 10.52. Found: C, 62.94; H, 5.18; N, 10.51%.
