Reaction Steps
Reaction of oxalyl chloride (70 λL, 0.8 mmol) and benzoic acid 53 (200 mg, 0.54 mmol) with subsequent reaction with 3-pyridinylmethylamine (60 λL, 0.6 mmol) gave benzamide 54 (171 mg, 68%) as a white powder: mp (EtOAc) 178-181° C.; 1H NMR δ 9.19 (t, J=5.9 Hz, 1H, CONH), 8.57 (d, J=1.6 Hz, 1H, H-2″), 8.47 (dd, J=4.8, 1.5 Hz, 1H, H-6″), 7.97 (dd, J=6.7, 1.8 Hz, 2H, H-2, H-6), 7.81 (dd, J=6.7, 1.8 Hz, 2H, H-3, H-5), 7.74 (ddd J=8.1, 2.1, 1.6 Hz, 1H, H-4″), 7.68 (s, 1H, H-5′), 7.65 (dd, J=8.3, 1.7 Hz, 2H, H-2′″, H-6″), 7.41 (br d, J=8.3 Hz, 2H, H-3′″, H-5″), 7.36 (ddd, J=8.1, 4.8, 0.7 Hz, 1H, H-5″), 4.87 (s, 2H, CH2SO2), 4.51 (d, J=5.9 Hz, 2H, CH2N), 2.40 (s, 3H, CH3); 13C NMR δ 165.7, 165.5, 148.9, 148.1, 145.2, 144.3, 135.9, 135.3, 135.2, 135.0, 134.9, 129.5 (2), 128.2 (2), 128.1 (2), 125.9 (2), 123.4, 122.2, 57.0, 40.5, 21.0; MS m/z 464.8 (MH+, 100%). Anal. calcd for C24H21N3O3S2: C, 62.18; H, 4.57; N, 9.06. Found: C, 62.30; H, 4.55; N, 9.10%.
