Triethylamine → N-[2-({2-[3-(4-cyano-3-fluoro-benzyl)-3H-imidazol-4-yl]-ethylamino}-methyl)-phenyl]-3-hydroxy-benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[5-(2-amino-ethyl)-imidazol-1-ylmethyl]-2-fluoro-benzonitrile dihydrochloride (Step F) (0.64 g, 2.03 mmol) in MeOH (15 mL) was added NEt3 dropwise to pH=4.5. To this solution was added N-(2-formyl-phenyl)-3-hydroxy-benzamide (0.64 g, 2.64 mmol) and NaCNBH3 (0.255 g, 4.06 mmol), and the reaction was stirred 18 h at 25° C. The MeOH was removed in vacuo, and the residue was partitioned with EtOAc and saturated NaHCO3. The organic layer was separated and washed 3× with 10% HCl. The acidic layers were combined, made basic with Na2CO3, then extracted 3× with EtOAc. These layers were combined, washed with brine and dried (MgSO4). Filtration and concentration in vacuo gave the crude product which was purified by prep HPLC to obtain the title compound.

Provenance & Evidence