Diethyl Ether → HCID 57677614, compound

Participants

Reaction Steps

To a solution of 3-[4-(4-amino-2-fluorophenoxy)pyridin-2-yl]-1-[1-(2-dimethylaminoethyl)piperidin-4-yl]-1-methylurea (61 mg) in tetrahydrofuran (3.0 ml) was added a solution of 2-phenylacetyl isocyanate in hexane (0.2 M, 1.70 ml) at room temperature, followed by stirring at room temperature for 9.5 hrs. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated to give a residue, which was then purified by silica gel column chromatography (FUJI Silysia NH, eluent; ethyl acetate, then ethyl acetate:methanol=10:1). Fractions containing a target compound were concentrated to give a residue, to which diethyl ether (1 ml) and hexane (1 ml) were added to give a precipitate. The precipitate was filtered off, and dried under aeration to provide the titled compound (17.8 mg, 21%) as white powder.

Provenance & Evidence