Reaction Steps
Reaction of oxalyl chloride (75 λL, 0.9 mmol) and benzoic acid 4 (215 mg, 0.6 mmol) with subsequent coupling to 2-pyridinylmethylamine (68 λL, 0.6 mmol) gave benzamide 8 (221 mg, 83%) as a white powder: mp (EtOAc) 154-155° C.; 1H NMR δ 9.21 (t, J=6.0 Hz, 1H, CONH), 8.52 (dd, J=4.8, 1.5 Hz, 1H, H-6′), 8.04 (d, J=8.6 Hz, 2H, H-2, H-6), 7.91 (d, J=8.6 Hz, 2H, H-3, H-5), 7.77 (dt, J=7.8, 1.8 Hz, 1H, H-4′), 7.67 (d, J=8.3 Hz, 2H, H-2″, H-6″), 7.42 (d, J=8.3 Hz, 2H, H-3″, H-5″), 7.35 (d, J=7.8 Hz, 1H, H-3′), 7.27 (dd, J=7.7, 4.8 Hz, 1H, H-5′), 4.63 (s, 2H, CH2SO2), 4.59 (d, J=6.0 Hz, 2H, CH2N), 2.41 (s, 3H, CH3), 2.14 (s, 3H, CH3); 13C NMR δ 165.6, 158.6, 158.0, 149.9, 148.8, 144.5, 136.7, 135.6, 135.5, 129.6 (2), 128.8, 128.3 (2), 128.1 (2), 126.0, 125.4 (2), 122.1, 121.0, 53.0, 44.8, 21.0, 9.7; MS m/z 462.6 (MH+, 100%). Anal. calcd for C25H23N3O4S: C, 65.06; H, 5.02; N, 9.10. Found: C, 65.03; H, 5.00; N, 9.11%.
