Reaction Steps
Reaction of oxalyl chloride (27 λL, 0.31 mmol) and benzoic acid 23 (85 mg, 0.21 mmol) with subsequent coupling to 3-pyridinylmethylamine (23 λL, 0.23 mmol) gave benzamide 24 (49 mg, 46%) as a white powder: mp (EtOAc) 177-180° C.; 1H NMR δ 9.20 (t, J=5.8 Hz, 1H, CONH), 8.57 (d, J=1.8 Hz, 1H, H-2′), 8.46 (dd, J=4.7, 1.5 Hz, 1H, H-6′), 7.98 (br d, J=8.5 Hz, 2H, H-2, H-6), 7.86 (br d, J=8.5 Hz, 2H, H-3, H-5), 7.73 (br dt, J=7.9, 1.9 Hz, 1H, H-4′), 7.70 (br dd, J=8.6, 1.9 Hz, 2H, H-2″, H-6″), 7.63 (br dd, J=8.6, 1.9 Hz, 2H, H-3″, H-5″), 7.36 (ddd, J=7.89, 4.7, 0.6 Hz, 1H, H-5′), 4.60 (s, 2H, CH2SO2), 4.51 (d, J=5.8 Hz, 2H, CH2N), 2.14 (s, 3H, CH3), 1.30 [s, 9H, C(CH3)3]; 13C NMR δ 165.4, 157.8, 157.0, 149.8, 148.7, 148.0, 135.4, 135.3, 135.0, 134.8, 128.7, 128.1 (2), 127.9 (2), 125.9 (2), 125.3 (2), 123.3, 52.9, 40.4, 34.8, 30.6 (3), 9.5, one resonance not observed; MS m/z 504.5 (MH+, 100%). Anal. calcd for C28H29N3O4S.CH3OH: C, 65.03; H, 6.21; N, 7.84. Found: C, 65.03; H, 5.94; N, 7.99%.
