Diisopropylethylamine → 4-((4-Fluorobenzyl)oxy)-1-(1-methyl-2-(1,3-oxazol-5-yl)-1H-benzimidazol-6-yl)pyridin-2(1H)-one

Participants

Reaction Steps

A mixture of 1-(4-amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (100 mg), oxazole-5-carboxylic acid (33.3 mg), HATU (118 mg), N,N-diisopropylethylamine (0.154 ml) and DMF (2 ml) was stirred at room temperature for 2 h. The mixture was poured into saturated NaHCO3 solution and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was dissolved in AcOH (2 ml), and the mixture was stirred at 80° C. for 2 h. The mixture was concentrate in vacuo. The residue was purified by NH silica gel column chromatography (MeOH/EtOAc). The resulting solid was washed with EtOAc/hexane to give the title compound (40.7 mg) as an off-white solid.

Provenance & Evidence