反应详情

Reaction of oxalyl chloride (195 λL, 2.2 mmol) and benzoic acid 4 (415 mg, 1.1 mmol) and subsequent coupling to 3-pyridinylmethylamine (125 λL, 1.2 mmol) gave benzamide 9 (406 mg, 79%) as a white powder: mp (EtOAc) 190-191° C.; 1H NMR δ 9.20 (t, J=5.8 Hz, 1H, CONH), 8.57 (d, J=1.7 Hz, 1H, H-2′), 8.47 (dd, J=4.8, 1.5 Hz, 1H, H-6′), 8.00 (d, J=8.5 Hz, 2H, H-2, H-6), 7.90 (d, J=8.4 Hz, 2H, H-3, H-5), 7.74 (dt, J=7.8, 1.8 Hz, 1H, H-4′), 7.67 (d, J=8.2 Hz, 2H, H-2″, H-6″), 7.42 (d, J=8.2 Hz, 2H, H-3″, H-5″), 7.36 (dd, J=7.8, 4.8 Hz, 1H, H-5′), 4.63 (s, 2H, CH2SO2), 4.51 (d, J=5.8 Hz, 2H, CH2N), 2.40 (s, 3H, CH3), 2.13 (s, 3H, CH3); 13C NMR δ 165.5, 158.0, 149.9, 148.9, 148.1, 144.5, 135.6, 135.4, 135.2, 134.9, 129.6 (2), 128.8, 128.3 (2), 128.1 (2), 126.0, 125.4 (2), 123.5, 53.0, 40.6, 21.0, 9.7; MS m/z 462.7 (MH+, 100%). Anal. calcd for C25H23N3O4S: C, 65.06; H, 5.02; N, 9.10. Found: C, 64.79; H, 5.03; N, 9.15%.