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0 °C

To a mixture of 4-[5-[2-(3-fluorophenyl)ethyl]-1,3,4-oxadiazol-2-yl]-N2-(4-methoxyphenyl)benzene-1,2-diamine (0.20 g, 0.49 mmol), 6 M hydrochloric acid (2.5 mL) and acetic acid (2.5 mL) was added an aqueous solution (0.25 mL) of sodium nitrite (41 mg, 0.59 mmol) at 0° C., and the obtained mixture was stirred at 0° C. for 30 min and at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=1/1) and recrystallized from hexane/ethyl acetate to give the title compound (51.2 mg, yield 25%) as colorless crystals.

1. washwashed with water and saturated brine
2. dry with materialdried over anhydrous magnesium sulfate
3. concentrationconcentrated under reduced pressure
4. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=1/1)
5. customrecrystallized from hexane/ethyl acetate