Phenylacetyl chloride → Phenylacetyl isothiocyanate

2-Phenylacetyl chloride (0.180 ml) was dissolved in acetonitrile (20 ml) under a nitrogen atmosphere, and then potassium thiocyanate (197 mg) was added thereto at 50° C., followed by stirring at the same temperature for 2 hrs. The reaction mixture was concentrated under a reduced pressure to give a residue, to which ethyl acetate (20 ml) and a saturated aqueous solution of sodium hydrogencarbonate (20 ml) were then added, followed by stirring for 30 min. The organic layer was separated, washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to provide 2-phenylacetyl isothiocyanate, which was used to prepare a solution in toluene (5 ml)-ethanol (5 ml). To the solution was added 4-(4-amino-2-fluorophenoxy)-2-[(4-hydroxypiperidin-1-yl)carbonylamino]pyridine (168 mg), followed by stirring overnight. The reaction mixture was concentrated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent; ethyl acetate:methanol=95:5). Fractions containing the target compound were concentrated to give a residue, to which diethyl ether (20 ml) was added to suspend. The resultant solid was filtered off and dried under aeration to provide the titled compound (106 mg, 42%) as white powder.

1. customat 50° C.
2. concentrationThe reaction mixture was concentrated under a reduced pressure
3. customto give a residue
4. stirringby stirring for 30 min
5. customThe organic layer was separated
6. washwashed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. customThe solvent was evaporated

ORD record

ord-bad0ef964477460fa6d668da0ebd1d64

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07531532B2