Reaction Steps
A mixture of 4-(aminomethyl)-N-(3-pyridinyl)benzamide (33) (250 mg, 1.1 mmol) and 6-chloro-3-pyridinesulfonyl chloride (233 mg, 1.1 mmol) in dry pyridine (10 mL) was stirred at 20° C. for 16 h. The solvent was evaporated and the residue stirred in ice/water (20 mL) for 1 h. The precipitate was filtered, washed with water (5 mL) and dried. The crude solid was purified by column chromatography, eluting with a gradient (0-30%) of MeOH/EtOAc, to give benzamide I-2 (279 mg, 63%) as a white powder: mp (MeOH/EtOAc) 226-228° C.; 1H NMR δ 10.36 (s, 1H, NHCO), 8.93 (d, J=2.2 Hz, 1H, H-2′), 8.75 (dd, J=2.6, 0.6 Hz, 1H, H-2″), 8.61 (br s, 1H, NHSO2), 8.32 (dd, J=4.6, 1.5 Hz, 1H, H-6′), 8.10-8.20 (m, 2H, H-4′, H-6″), 7.90 (br d, J=8.3 Hz, 2H, H-2, H-6), 7.72 (dd, J=8.4, 0.6 Hz, 1H, H-5″), 7.36-7.42 (m, 3H, H-3, H-5, H-5′), 4.19 (s, 2H, CH2N); 13C NMR δ 165.4, 153.6, 147.7, 144.6, 142.0, 141.2, 137.9, 136.6, 135.8, 133.1, 127.8 (2), 127.6 (2), 127.3, 125.0, 123.5, 45.7; MS m/z 404.0 (MH+, 100%), 406.0 (MH+, 60%). Anal. calcd for C18H15ClN4O3S: C, 53.67; H, 3.75; N, 13.91. Found: C, 53.37; H, 3.81; N, 14.03%.
