1,2-Dichloroethane → HCID 178522419, compound

Participants

Reaction Steps

2-(2-Pyrrolidin-1-yl-ethoxy)-benzoic acid methyl ester (125 mg, 0.50 mmol) and lithium hydroxide (21 mg, 0.50 mmol) were dissolved in THF/H2O (1:1, 2 ml) and the mixture stirred at ambient temperature for 20 h. The reaction mixture was reduced in vacuo and azeotroped with toluene (3×5 ml) to give a white solid, which was dissolved in water (1 ml) and acidified with 2 M aqueous HCl (1 ml). The resulting solution was reduced in vacuo and azeotroped with toluene (3×5 ml) to give a pale yellow gel, which was combined with 3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (100 mg, 0.50 mmol), EDC (116 mg, 0.60 mmol) and HOBt (81 mg, 0.60 mmol) and stirred at ambient temperature in DMF (3 ml) for 20 h. The reaction mixture was reduced in vacuo and purified by flash column chromatography [SiO2, CH2Cl2/MeOH (95:5, 87.5:12.5) then 120 DMAW] to give N-[3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-2-(2-pyrrolidin-1-yl-ethoxy)-benzamide (63 mg, 30%) as a pale pink solid. (LC/MS: Rt 2.08, [M+H]+ 417.11).

Provenance & Evidence