Reaction Steps
Reaction of oxalyl chloride (92 λL, 1.06 mmol) and benzoic acid 41 (294 mg, 0.70 mmol) with subsequent coupling to 3-pyridinylmethylamine (78 λL, 0.77 mmol) gave benzamide 42 (263 mg, 74%) as a white powder: mp (EtOAc) 104-108° C.; 1H NMR δ 9.23 (t, J=5.9 Hz, 1H, CONH), 8.57 (d, J=1.6 Hz, 1H, H-2′), 8.46 (dd, J=4.7, 1.5 Hz, 1H, H-6′), 8.01 (d, J=8.5 Hz, 2H, H-2, H-6), 7.92 (d, J=8.5 Hz, 2H, H-3, H-5), 7.74 (br d, J=7.5 Hz, 1H, H-4′), 7.37 (dd, J=7.5, 4.8 Hz, 1H, H-5′), 7.33 (dd, J=8.5, 2.1 Hz, 1H, H-6″), 7.25 (d, J=2.1 Hz, 1H, H-2″), 7.14 (d, J=8.5 Hz, 1H, H-5″), 4.63 (s, 2H, CH2SO2), 4.51 (d, J=5.8 Hz, 2H, CH2N), 3.84 (s, 3H, OCH3), 3.76 (s, 3H, OCH3), 2.15 (s, 3H, CH3); 13C NMR δ 165.5, 157.9, 153.1, 149.9, 148.8, 148.6, 148.0, 135.3, 135.1, 134.8, 129.7, 128.8, 128.0 (2), 126.2, 125.3 (2), 123.4, 122.2, 111.2, 110.6, 55.9, 55.7, 52.9, 40.4, 9.6; MS m/z 508.7 (MH+, 100%). Anal. calcd for C26H25N3O6S.¾CH3OH: C, 60.44, 5.31; N, 7.90. Found: C, 60.58; H, 5.17; N, 7.63%.
