2-Methylbenzenesulfonamide → 2-[(1,3-diphenyl-1H-pyrazol-5-yl)amino]-5-methoxy-N-[(2-methylphenyl)sulfonyl]benzamide

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To a solution of 2-[(1,3-diphenyl-1H-pyrazol-5-yl)amino]-5-methoxybenzoic acid (Example 29) (100 mg, 0.26 mmol) in dichloromethane (3 mL) were added o-toluenesulfonamide (53.3 mg, 0.31 mmol), EDCI (99.47 mg, 0.52 mmol), DMAP (63.40 mg, 0.52 mmol), and triethylamine (0.127 mL, 0.91 mmol). The reaction mixture was stirred for 2 h, and then diluted with dichloromethane (10 mL) and water (20 mL). The organic phase was separated and then washed with brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography using 90% EtOAc/hexane, to afford the product (13.9 mg, 10.0%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 2.56 (s, 3H), 3.74 (s, 3H) 6.67 (s, 1H), 7.03 (dd, 2H), 7.26-7.60 (m, 14H), 7.84 (dd, 2H), 7.94 (d, 1H). ES-MS m/z 539.1 (MH+); HPLC RT (min) 3.71.

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