Triethylamine → HCID 53260082, compound

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Reaction Steps

A mixture of 1-(8-{2-[4-(4-chloro-3-fluoro phenyl)piperidin-4-yl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole dihydrochloride (0.40 g, 0.78 mmol), triethylamine (0.35 mL, 2.5 mmol) and 4-chloro-3-sulfamoylbenzoic acid (184 mg, 0.78 mmol) in dimethylformamide (2.5 mL) was treated with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (327 mg, 0.86 mmol) and the resulting mixture was stirred for 1 h at rt. The mixture was diluted with water and the resulting precipitate was collected, washed with saturated sodium bicarbonate solution, with water, dried and purified by chromatography on silica gel eluting with a 400:15:1 to 200:15:1 gradient of chloroform:methanol:ammonium hydroxide to give 2-chloro-5-[(4-(4-chloro-3-fluoro phenyl)-4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}piperidin-1-yl)carbonyl]benzenesulfonamide as a solid (0.24 g, 43%). 1H NMR (400 MHz, CD3OD) δ 8.09 (s, 1H), 7.68 (m, 1H), 7.61 (m, 1H), 7.34-7.54 (m, 4H), 7.17-7.26 (m, 3H), 4.73 (m, 1H), 4.09 (m, 1H), 3.59 (m, 1H), 3.43 (m, 1H), 3.30 (m, 3H), 2.53 (s, 3H), 2.40-2.48 (m, 4H), 2.28 (m, 1H), 2.16 (m, 1H), 1.83-2.04 (m, 10H), 1.70 (m, 2H). HRMS C35H38Cl2FN5O3S m/z 698.2135 (M+H)Cal., 698.2142 (M+H)Obs..

Provenance & Evidence