Benzene → HCID 178437536, compound

Participants

Reaction Conditions

Reaction Steps

A mixture comprising benzyl 2-(1-ethoxycarbonylethyl)-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate (6.37 g, 0.018 mol), 4-amino-3-(N-methylamino)benzoic acid (2.70 g, 0.016 mol) and DMPU (20 mL) was degassed briefly on a vacuum line, heated heated at 185° C. under nitrogen for 4 hours, cooled and combined with an equivalent volume of benzene. Ether was then added to the mixture to give a precipitate. The precipitate was isolated by filtration, dried briefly on a vacuum line and further purified by a reprecipitation from hot ethanol/water. The precipitate was isolated recovered by filtration and dried to provided 2-[1-(5-benzyloxycarbonyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl)ethyl]-3-methyl-3H-benzoimidazole-5-carboxylic acid (4.73 g, 58%); 1H-NMR (300 MHz, DMSO-d6) d ppm: 12.70 (br s, 1H), 11.80 (s, 1H), 8.15 (s, 1H), 7.78 (d, 1H, J=8.3 Hz), 7.64 (d, 1H, J=8.3 Hz), 7.31 (s, 5H), 5.09 (s, 2H), 4.66 (q, 1H, J=5.2 Hz), 4.32 (br s, 2H), 3.78 (s, 3H), 3.65 (br s, 2H), 2.52 (br s, 2H), 1.73 (d, 3H, J=5.2 Hz).

Provenance & Evidence