Reaction Steps
Reaction of oxalyl chloride (71 λL, 0.82 mmol) and benzoic acid 4 (202 mg, 0.54 mmol) with subsequent reaction with 2-(3-pyridinyl)ethylamine (71 λL, 0.59 mmol) gave benzamide 12 (208 mg, 81%) as a white powder: mp (EtOAc) 207-208° C.; 1H NMR δ 8.68 (t, J=5.6 Hz, 1H, CONH), 8.46 (d, J=1.7 Hz, 1H, H-2′), 8.41 (dd, J=4.7, 1.6 Hz, 1H, H-6′), 7.93 (dd, J=8.6, 2.0 Hz, 2H, H-2, H-6), 7.87 (dd, J=8.6, 2.0 Hz, 2H, H-3, H-5), 7.65-7.69 (m, 3H, H-4′, H-2″, H-6″), 7.42 (d, J=8.3 Hz, 2H, H-3″, H-5″), 7.31 (ddd, J=7.8, 4.7, 0.7 Hz, 1H, H-5′), 4.62 (s, 2H, CH2SO2), 3.54 (dt, J=7.0, 5.8 Hz, 2H, CH2N), 2.89 (t, J=7.1 Hz, 2H, CH2), 2.40 (s, 3H, CH3), 2.13 (s, 3H, CH3); 13C NMR δ 165.4, 158.0, 149.9, 149.8, 147.4, 144.5, 136.2, 135.8, 135.6, 134.9, 129.6 (2), 128.7, 128.3 (2), 127.9 (2), 126.0, 125.4 (2), 123.4, 53.0, 40.4, 32.0, 21.0, 9.7; MS m/z 476.6 (MH+, 100%). Anal. calcd for C26H25N3O4S: C, 65.67; H, 5.30; N, 8.84. Found: C, 65.53; H, 5.18; N, 8.75%.
