4-Methylmorpholine → Ammonium Hydroxide

Participants

Reaction Steps

To a solution of 4-(5-aminomethyl-imidazol-1-ylmethyl)-2-fluoro-benzonitrile dihydrochloride (0.17 g, 0.651 mmol) in DMF (5.0 mL) was added cyclohexylacetic acid (0.11 g, 0.782 mmol), BOP reagent (0.433 g, 0.977 mmol), and NMM (0.28 mL, 2.6 mmol). The mixture was stirred for 18 hr. The DMF was removed in vacuo and the residue was partitioned with EtOAc and saturated NaHCO3 solution. The EtOAc layer was washed with H2O, brine, and dried (MgSO4). Filtration and concentration in vacuo gave the title compound after chromatography (silica gel, CH2Cl2:CH3OH:NH4OH/97:3:0.3).

Provenance & Evidence