Water → HCID 86605791, compound

Participants

Reaction Steps

To a solution of tetraethyl methylenediphosphonate (215 mg) in N,N-dimethylformamide (5 mL) was added sodium hydride (60% in oil, 38 mg), and the mixture was stirred at room temperature for 20 min. A solution of N-(4-formyl-1-phenyl-1H-pyrazol-3-yl)-3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzamide (433 mg) in N,N-dimethylformamide (5 mL) was added to the reaction mixture, and the mixture was stirred at room temperature for 2 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with distilled water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give diethyl (E)-2-[3-({3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoyl}amino)-1-phenyl-1H-pyrazol-4-yl]ethenylphosphonate as colorless amorphous form (205 mg, yield 38%) from a fraction eluted with ethyl acetate-hexane (1:1 to 1:0, v/v).

Provenance & Evidence