Methanol → 1-(4-{[3-(hydroxymethyl)cyclobutyl]oxy}phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide

Participants

Reaction Conditions

Reaction Steps

Methyl 3-(4-{5-[(pyridin-3-ylmethylamino)carbonyl]-1H-benzimidazol-1-yl}phenoxy)cyclobutanecarboxylate (150 mg, 0.33 mmol) and sodium borohydride (25 mg, 0.66 mmol) were dissolved in THF (3 mL), put under a N2 atmosphere, and heated to 60° C. Methanol (13 μL, 0.33 mmol) was then added and the reaction was stirred at 60° C. for 48 h. The reaction was cooled to rt and concentrated in vacuo. Methanol (2 mL) was then added followed by sodium hydroxide (3M, 5 mL) and the methanol was removed in vacuo. The resultant aqueous solution was extracted with ethyl acetate (3×), dried over MgSO4, filtered, and concentrated in vacuo. The crude solid was purified using the Waters mass-directed HPLC purification system to provide 1-(4-{[3-(hydroxymethyl)cyclobutyl]oxy}phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide as a white solid. MS (ES+): m/z 429 (90) [MH+].

Provenance & Evidence