Diethyl Ether → HCID 23153024, compound

Participants

Reaction Steps

1-[4-(4-Aminophenoxy)pyridin-2-yl]-3,3dimethylurea (30 mg) was dissolved in N,N-dimethylformamide (1 ml) under a nitrogen atmosphere, and then N-(4-fluorophenyl)malonic acid (65.1 mg), triethylamine (0.046 ml) and (1H-1,2,3-benzotriazol-1-yloxy)[tri(dimethylamino)]phosphonium hexafluorophosphate (146 mg) were added thereto at 50° C., followed by stirring at the same temperature for 1.5 hr. The reaction mixture was cooled down to room temperature, and partitioned between ethyl acetate and a 1 N aqueous solution of sodium hydroxide. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, a saturated aqueous solution of ammonium chloride, water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then purified by silica gel column chromatography (FUJI Silysia NH, eluent; hexane:ethyl acetate=1:5 to 1:8). Fractions containing the target compound were concentrated to give a residue, to which diethyl ether (2 ml)-hexane (2 ml) was added to suspend. The solid was filtered off and dried under aeration to provide the titled compound (43.4 mg, 87.4%) as a white solid.

Provenance & Evidence