Triethylamine → HCID 58728137, compound

Participants

Reaction Steps

A mixture of 1-(8-{2-[4-(1,3-benzodioxol-5-yl)piperidin-4-yl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole dihydrochloride (0.20 g, 0.39 mmol), triethylamine (0.17 mL, 1.25 mmol) and 2,2-dimethyl-3-hydroxypropionic acid (46 mg, 0.39 mmol) in dimethylformamide (1.25 mL) was treated with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (163 mg, 0.43 mmol) and the resulting mixture was stirred for 1 h at rt. The mixture was diluted with water and the resulting gummy precipitate was dissolved in dichloromethane, washed with saturated sodium bicarbonate solution, with water, dried and purified by chromatography on silica gel eluting with a dichloromethane to methanol-dichloromethane 1:9 gradient to give 3-(4-(1,3-benzodioxol-5-yl)-4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}piperidin-1-yl)-2,2-dimethyl-3-oxopropan-1-ol as a solid (0.13 g, 59%). 1H NMR (400 MHz, CDCl3) δ 7.66 (m, 1H), 7.29 (m, 1H), 7.15 (m, 2H), 6.80 (m, 2H), 6.73 (m, 1H), 5.97 (s, 2H), 4.62 (m, 1H), 3.92 (m, 2H), 3.75 (m, 1H), 3.46 (s, 2H), 3.26 (m, 4H), 2.57 (s, 3H), 2.38 (m, 2H), 2.14 (m, 2H), 1.91-2.00 (m, 6H), 1.70-1.78 (m, 4H), 1.64 (m, 2H), 1.25 (s, 6H). HRMS C34H44N4O4 m/z 573.3441 (M+H)Cal. 573.3428 (M+H)Obs..

Provenance & Evidence