[BH4-].[Na+].[NH2:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=1[C:12](=O)[CH3:13].[S-:15][C:16]#[N:17].[K+].Cl>C(O)C.O>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[NH:3][C:16](=[S:15])[NH:17][CH:12]2[CH3:13]
Under an atmosphere of nitrogen and at a temperature of 65° C., sodium borohydride (154 mg, 4 mmol) was added to a solution of 1-(2-amino-3-methoxy-phenyl)-ethanone (960 mg, 6 mmol) in ethanol (8 ml). After stirring at 65° C. overnight, water (5 ml), a solution of potassium thiocyanate (620 mg, 6 mmol) in water (3 ml), and a solution of conc. HCl (3 ml) in water (4 ml) were added subsequently. The mixture was then stirred for an additional 3 h at 65° C. Upon cooling, the solvent was evaporated and the residue was taken up in water/ethyl acetate. The organic phase was dried (Na2SO4), and the solvent was evaporated. Chromatography (silica gel, heptan/ethyl acetate=100/0-70/30) gave the title compound (700 mg, 58%).
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