Trifluoroacetic acid → HCID 68512218, compound

Participants

Reaction Steps

4-(2-ethoxy-5-methylbenzoimidazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (367 mg, 1.02 mmol) was dissolved in CH2Cl2 (2 mL) and TFA (1 mL) and the solution was stirred at rt for 1 hour. The mixture was evaporated to dryness and the residue was extracted with CH2Cl2, brine and 2N NaOH solution. The organic layer was washed with brine and dried over Na2SO4. After the evaporation of solvents, an oily residue was obtained (217 mg, 0.84 mmol) as 4-(2-ethoxy-5-methylbenzoimidazol-1-yl)-piperidine which was then was mixed with (S)-(2-iodomethyl-indan-5-yl)-carbamic acid tert-butyl ester (224 mg, 0.60 mmol) and cesium carbonate (817 mg, 2.51 mmol) in acetonitrile (10 mL). The mixture was stirred at 85° C. for 16 hrs. The reaction mixture was filtered and solvents were evaporated. The residue was purified through a Biotage flash column chromatography using 5% CH3OH in CH2Cl2 to give a brownish fluffy material (206 mg, 68%) as (S)-{2-[4-(2-ethoxy-5-methylbenzoimidazol-1-yl)-piperidin-1-ylmethyl]-indan-5-yl}-carbamic acid tert-butyl ester.

Provenance & Evidence