Diethyl Ether → HCID 57677657, compound

Participants

Reaction Steps

4-(1-Methylpiperidin-4-yl)piperazine-1-carboxylic acid [6-(4-amino-2-fluorophenoxy)pyrimidin-4-yl]amide (110 mg) was dissolved in ethanol (1 ml), and then (S)-(+)-10-camphorsulfonic acid (60 mg) was added thereto, followed by stirring for 5 min. A 0.25 M solution of 2-phenylacetyl isothiocyanate in toluene (1.54 ml) was added thereto, followed by stirring for 1 hr. The reaction mixture was partitioned between ethyl acetate (30 ml) and a saturated aqueous solution of sodium hydrogencarbonate (20 ml). The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (20 ml), water (20 ml), brine (20 ml) 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; heptane:ethyl acetate=1:5 to 1:10, then ethyl acetate). Fractions containing the target compound were concentrated to give a residue, to which diethyl ether (1.5 ml) and hexane (3.0 ml) were then added to suspend. The solid was filtered off, and dried under aeration to provide the titled compound (24.3 mg, 15.6%) as white powder.

Provenance & Evidence