Acetic Acid → HCID 25070630, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-methyl-1-piperidin-4-yl-1H-benzoimidazole-5-carboxylic acid allyl ester dihydrochloride (55.8 mg, 0.15 mmol, 1.0 equiv; intermediate A1) in methanol (0.8 mL) and water (0.4 mL) was added a solution of 10 M NaOH (60 μL), acetic acid (86 μL, 90.3 mg, 1.50 mmol, 10 equiv), 3-ethoxy-4-fluoro-benzaldehyde (30.3 mg, 0.18 mmol, 1.2 equiv; intermediate B1, vide infra) and sodium cyanoborohydride (47.1 mg, 0.75 mmol, 5.0 equiv), dissolved in ethanol (0.5 mL). The reaction mixture was stirred at 70° C. overnight. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 13.4 mg (22%) of the title compound. MS (ISP): 412.3 [M+H]+.

Provenance & Evidence