Acetic Acid → 2-Fluoro-4-(5-{[2-(3'-hydroxybiphenyl-2-yl)ethylamino]methyl}imidazol-1-ylmethyl)benzonitrile

Participants

Reaction Steps

1-amino-2-(3′-hydroxybiphenyl-2-yl)ethane hydrochloride from Step C (0.47 mmol) and 1-(4-cyano-3-fluorobenzyl)-5-imidazolecarboxaldehyde from Example 3, Step G (112 mg, 0.49 mmol) were stirred in MeOH (1 mL) for 20 min, then NaCNBH3 (38 mg, 0.60 mmol) was added. The reaction mixture was adjusted to pH 5 with AcOH, as judged from wetted pH paper, and stirring was continued at ambient temperature for 18 hours. The reaction was quenched with 10% aq. citric acid and stirred for 20 min. Sat. aq. NaHCO3 (10 mL) was added and the mixture was extracted with CH2Cl2 (3×20 mL).

Provenance & Evidence