Reaction Steps
Reaction of oxalyl chloride (111 λL, 1.27 mmol) and benzoic acid 4 (318 mg, 0.85 mmol) with subsequent coupling to (1-methyl-1H-imidazol-5-yl)methylamine (104 mg, 0.94 mmol) gave benzamide 15 (325 mg, 82%) as a white powder: mp (EtOAc) 240-242° C.; 1H NMR δ 8.93 (t, J=5.3Hz, 1 H, CONH), 7.97 (br d, J=8.5Hz, 2 H, H-2, H-6), 7.87 (br d, J=8.5Hz, 2 H, H-3, H-5), 7.67 (br d, J=8.3 Hz, 2 H, H-2′, H-6′), 7.54 (s, 1 H, H-2″), 7.42 (br d, J=8.3Hz, 2 H, H-3′, H-5′), 6.84 (s, 1 H, H-4″), 4.62 (s, 2 H, CH2SO2), 4.48 (d, J=5.3Hz, 2 H, CH2N), 3.62 (s, 3 H, NCH3), 2.40 (s, 3 H, CH3), 2.13 (s, 3 H, CH3); 13C NMR δ 165.1, 157.9, 149.8, 144.4, 138.1, 135.5, 135.4, 129.5 (2), 128.7, 128.6, 128.1 (2), 128.0 (2), 127.7, 125.9, 125.2 (2), 52.8, 32.5, 30.9, 20.9, 9.5; MS m/z 465.5 (MH+, 100%). Anal. calcd for C24H24N4O4S: C, 62.05; H, 5.21; N, 12.06. Found: C, 62.42; H, 5.24; N, 12.12%.
