4-Toluenesulfonyl chloride → HCID 67012524, compound

Participants

Reaction Steps

A mixture of 1-(3-aminophenyl)-N-(pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide dihydrochloride (47 mg, 0.14 mmol) and TsCl (27 mg, 0.14 mmol) was dissolved in anhydrous THF (3 mL) at 0° C. and treated with Et3N (95 μL, 0.68 mmol). The reaction mixture was stirred for 72 h and then filtered. The solid residue was washed with THF and the combined washings and filtrate were concentrated in vacuo. The resultant residue was purified by silica gel chromatography (0-7% MeOH in CH2Cl2). Further purification was achieved by trituration with MeOH to afford 1-(3-{[(4-methylphenyl)sulfonyl]amino}phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide as a white solid. 1H-NMR (DMSO-d6, 400 MHz): δ 2.35 (s, 3H), 4.54 (d, J=5.6 Hz, 2H), 7.20 (d, J=8.0 Hz, 1H), 7.32-7.44 (m, 4H), 7.50 (t, J=7.6 Hz, 1H), 7.68-7.81 (m, 3H), 7.89 (d, J=8.8 Hz, 1H), 8.36 (s, 1H), 8.47 (brs, 1H), 8.61 (s, 1H), 9.19 (brs, 1H). MS (ES+): m/z 498 [MH+].

Provenance & Evidence