Potassium Carbonate → HCID 18474011, compound

Participants

Reaction Steps

A mixture of the compound (163 mg) obtained in Example 7d, 10% palladium-carbon (20 mg) and methanol (10 ml) was stirred at room temperature for 6 hours under a hydrogen atmosphere. The reaction mixture was filtered to remove the palladium-carbon and the resulting filtrate was concentrated at reduced pressure. Acetone (10 ml) was added to the resulting residue and benzoyl isothiocyanate (0.064 ml) was then added dropwise at room temperature. The reaction mixture was stirred at room temperature for 16 hours and then water was added, followed by extraction with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate and then concentrated at reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:3) to give N-benzoyl-N′-(3-((tert-butoxycarbonyl)aminomethyl)-2-methyl-4-(pyrazol-1-yl)phenyl)thiourea (yield, 78%). A mixture of the resulting thiourea compound (143 mg), potassium carbonate (64 mg) and methanol (4 ml) was stirred at room temperature for 2 hours. The reaction mixture was concentrated at reduced pressure and water was added to the resulting residue, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried with anhydrous magnesium sulfate and then concentrated at reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:2) to give the titled compound quantitatively.

Provenance & Evidence