Acetic Acid → HCID 10111242, compound

Participants

Reaction Steps

4-[2-(5-Methoxy-benzoimidazol-1-yl)-quinolin-8-yl]-benzaldehyde 5A (120 mg, 0.32 mMol) was dissolved in 2 mL of methanol under an atmosphere of dry N2. To this solution was added 800 μL of a solution of 2.0 M methylamine in methanol and then acetic acid (AcOH) was added dropwise until the pH of the solution was ˜5. To this solution was added (42 mg, 0.64 mMol) sodium cyanoborohydride (NaCNBH3) and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was then concentrated under vacuum and subsequently partitioned between DCM and 0.1 N aqueous NaOH. The DCM layer was washed again with 0.1 N aqueous NaOH, then dried over MgSO4, filtered and concentrated under vacuum to give 220 mg of a green residue. The residue was chromatographed on flash silica gel eluting with a gradient DCM/MeOH (595) to DCM/MeOH (15/85) to DCM/MeOH/NH4OH (1584.50.5) to give 50 mg of a white solid of the title compound 5.

Provenance & Evidence