Triethylamine → HCID 178490316, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6-(carboxymethyl)-2-(2-methoxyphenyl)-1H-benzimidazole-7-carboxylic acid (800 mg, 2.45 mmol) and tert-butyl (3-aminopropyl)[2-(3,4-dimethoxyphenyl)ethyl]carbamate (1.00 g, 2.94 mmol) in ethyleneglycol (6.1 mL) was heated at 180° C. for 1 h. The cooled mixture was dissolved in EtOAc (500 mL) and the resulting solution was washed with water (2×100 mL) and brine (200 mL), dried (MgSO4) and concentrated under reduced pressure. A solution of the resulting yellow solid (1.04 g) and aqueous 1 N HCl solution (33 mL) in MeOH (100 mL) was heated at 70° C. for 16 h. The mixture was concentrated under reduced pressure. (BOC)2O (1.34 g, 6.12 mmol) and Et3N (2.06 g, 20.4 mmol) were successively added to a solution of the residue in CH2Cl2 (30 mL). The mixture was stirred at room temperature for 15 min then was diluted with CH2Cl2 (300 mL). The resulting solution was washed with water (2×100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (10-40μ silica gel; hexane:EtOAc 1:2 to 1:3) to give the title compound (839 mg, 54% yield) as a yellow solid.

Provenance & Evidence