Reaction Steps
Reaction of oxalyl chloride (56 λL, 0.64 mmol) and benzoic acid 32 (158 mg, 0.43 mmol) with subsequent coupling to 3-pyridinylmethylamine (48 λL, 0.47 mmol) gave benzamide 33 (79 mg, 40%) as a white powder: mp (EtOAc) 179-181° C.; 1H NMR δ 9.20 (t, J=5.8 Hz, 1H, CONH), 8.57 (d, J=1.8 Hz, 1H, H-2′), 8.47 (dd, J=4.7, 1.6 Hz, 1H, H-6′), 8.00 (d, J=8.5 Hz, 2H, H-2, H-6), 7.90 (br d, J=8.5 Hz, 2H, H-3, H-5), 7.74 (dt, J=7.9, 1.9 Hz, 1H, H-4′), 7.63 (br s, 1H, H, H-2″) 7.53-7.60 (m, 2H, H-4″, H-6″), 7.50 (t, J=7.6 Hz, 1H, H-5″), 7.36 (ddd, J=7.9, 4.7, 0.5 Hz, 1H, H-5′), 4.65 (s, 2H, CH2SO2), 4.51 (d, J=5.8 Hz, 2H, CH2N), 2.37 (s, 3H, CH3), 2.16 (s, 3H, CH3); 13C NMR δ 165.4, 157.9, 149.9, 148.8, 148.0, 139.0, 138.3, 135.3, 135.1, 134.8, 134.3, 128.9, 128.7, 128.3, 128.0 (2), 125.8, 125.3 (2), 125.2, 123.3, 52.8, 40.4, 20.6, 9.67; MS m/z 462.8 (MH+, 100%). Anal. calcd for C25H23N3O4S: C, 64.06, 5.02; N, 9.10. Found: C, 64.76; H, 5.06; N, 9.05%.
