Diethyl Ether → HCID 23153219, compound

Participants

Reaction Steps

4-(4-Amino-2-chlorophenoxy)-2-[(pyrrolidin-1-yl)carbonylamino]pyridine (99 mg) was dissolved in N,N-dimethylformamide (2 ml) under a nitrogen atmosphere, and then N-(4-fluorophenyl)malonic acid (176 mg), triethylamine (0.124 ml) and (1H-1,2,3-benzotriazol-1-yloxy)[tri(dimethylamino)]phosphonium hexafluorophosphate (394 mg) were added thereto at 50° C., followed by stirring at the same temperature for 30 min. 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, 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; ethyl acetate, then ethyl acetate:ethanol=95:5). Fractions containing the target compound were concentrated to give a residue, to which diethyl ether was added to suspend. The solid was filtered off and dried under aeration to provide the titled compound (102.9 mg, 67.7%) as white powder.

Provenance & Evidence