Water → HCID 86672709, compound

Participants

Reaction Steps

To a stirred solution of methyl 1-(2,2-dimethoxyethyl)-2-isopropyl-1H-benzo[d]imidazole-7-carboxylate from Step A above in methylene chloride and water was added trifluoroacetic acid and the reaction was stirred at room temperature for 1.5 h and then heated at reflux for 2 h. The reaction mixture was concentrated under reduced pressure to remove the excess trifluoroacetic acid, diluted with methylene chloride, washed with saturated aqueous sodium bicarbonate, re-extracted with methylene chloride, dried (Na2SO4), filtered, and concentrated under reduced pressure to give methyl 2-isopropyl-1-(2-oxoethyl)-1H-benzo[d]imidazole-7-carboxylate: 1H NMR (300 MHz, DMSO-d6) δ 9.69 (s, 1H), 7.87 (dd, J=8.1, 0.9 Hz, 7.68 (dd, J=7.5, 0.9 Hz, 1H), 7.26 (t, J=7.8 Hz, 1H), 5.44 (s, 2H), 3.84 (s, 3H), 3.22-3.17 (m, 1H), 1.34-1.27 (m, 6H); MS (ESI+) m/z 261 (M+H).

Provenance & Evidence