Phenylacetyl chloride → Pyrrolidine-1-carboxylic acid {4-[2-methyl-4-(3-phenylacetylthioureido)phenoxy]pyridin-2-yl}amide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-phenylacetyl chloride (0.0549 ml) in acetonitrile (5.0 ml) was added potassium thiocyanate (37.3 mg, 0.384 mmol), followed by stirring under a nitrogen atmosphere at 50° C. for 1 hr. The reaction mixture was cooled down to room temperature, and then pyrrolidine-1-carboxylic acid [4-(4-amino-2-methylphenoxy)pyridin-2-yl]amide (80 mg) was added thereto, followed by stirring under a nitrogen atmosphere for 21 hrs. The reaction mixture was partitioned between ethyl acetate (100 ml) and water (40 ml). The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then purified by silica gel column chromatography (eluent; ethyl acetate). Fractions containing the target compound were concentrated to give a solid, which was suspended in diethyl ether (4 ml). The solid was filtered off, and dried under aeration to provide the titled compound (51 mg, 41%) as colorless powder.

Provenance & Evidence