Sodium Sulfate → HCID 86680416, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (E)-3-(2-oxo-1-((2-(trimethylsilyl)ethoxy)methyl)-1,2-dihydroquinolin-6-yl)acrylic acid (80 mg, 0.232 mmol) and HATU (132 mg, 0.347 mmol) in DMF (2 ml) was added TEA (0.097 mL, 0.695 mmol). The reaction mixture was stirred for 30 minutes. A solution of (E)-1-(4-(difluoromethoxy)-2-methylphenyl)-2-hydroxyguanidine (80 mg, 0.347 mmol) in DMF was then added to and stirred at room temperature for 1 h. Sodium sulfate (99 mg, 0.695 mmol) was added and the reaction mixture was heated at 90° C. overnight. Water was added and the mixture was extracted with ethyl acetate (2×50 mL). The organic layer was dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography on silica gel using 10-12% chloroform in ethyl acetate to obtain (E)-6-(2-(3-((4-(difluoromethoxy)-3-methylphenyl)amino)-1,2,4-oxadiazol-5-yl)vinyl)quinolin-2(1H)-one (65 mg, 52%). LCMS, RT 2.298 min; LCMS (ES-API), m/z 541.

Provenance & Evidence