Diisopropylethylamine → 1-(6-(4-((4-Fluorobenzyl)oxy)-2-oxopyridin-1(2H)-yl)-1-methyl-1H-benzimidazol-2-yl)cyclopropanecarbonitrile

Participants

Reaction Steps

To a solution of 1-(4-amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (73 mg), 1-cyanocyclopropanecarboxylic acid (25.1 mg) and N,N-diisopropylethylamine (0.11 ml) in DMF (2 ml) was added HATU (86 mg), and the mixture was stirred at room temperature overnight. The mixture was poured into a mixture of EtOAc and water, and the organic layer was washed with brine, dried over MgSO4, and concentrated. Then the resulting residue was heated in AcOH (1 ml) at 90° C. for 1 h. The mixture was concentrated, and poured into saturated NaHCO3. The mixture was extracted with EtOAc, and the organic layer was washed with brine, dried over MgSO4, concentrated, and purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (8 mg) as a white solid.

Provenance & Evidence