Hydrochloric Acid → HCID 67237942, compound

Participants

Reaction Steps

To a solution of tert-butyl {3-[6-(pyridin-3-ylcarbamoyl)-2-(trimethoxymethyl)-1H-benzimidazol-1-yl]propyl}carbamate (85 mg, 0.17 mmol) in methanol (2 mL) was added concentrated HCl (1 mL). The solution is stirred at room temperature for 2 h and is evaporated to dryness. The residue is dissolved in methanol (5 mL), triethylamine (0.14 mL, 1.0 mmol) added, and the solution heated at reflux for 2 h. The cooled solution was diluted with CH2Cl2, and washed with Na2CO3. The organic layer was dried (MgSO4) and evaporated. The crude product was purified via preparative HPLC. The major peak was collected by passing the HPLC fractions, without concentrating, directly through an SCX cartridge (Silicycle tosic acid, 1 g). The cartridge was washed with methanol, then CH2Cl2/methanol (50:50). Finally, the product was eluted with CH2Cl2/methanol containing 1% NH4OH. The solution containing product was evaporated to afford the title compound (13 mg, 22%).

Provenance & Evidence