Benzoylhydrazine → HCID 178420151, compound

Participants

Reaction Conditions

Reaction Steps

2-Phenyl-pyrimidine-5-carbonitrile (Biofine International, 0.10 g, 0.55 mmol) and benzoic hydrazide (Aldrich, 0.075 g, 0.55 mmol) were dissolved in o-xylene (5 mL) and heated to 200° C. in a sealed pressure tube while stirring for 24 hours. After cooling to room temperature, the reaction mixture was heated to 200° C. in an open vessel under a stream of nitrogen for six hours. The remaining crude solid was dissolved in a minimal amount of 98:2 v/v dichloromethane-methanol and purified by flash silica column chromatography. Elution through a 40-g Analogix® flash silica cartridge with 100% dichloromethane to 2% methanol in dichloromethane afforded the title compound as a pale yellow solid (10 mg, 6% yield); Rf 0.1 with 98:2 v/v dichloromethane-methanol; melting point 280-282° C.; 1H-NMR (400 MHz; CDCl3) δ 8.48-8.42 (m, 2H), 8.12-8.06 (m, 2H), 7.60-7.48 (m, 6H); MS (ESI+) m/z 300.1 (M+1); H-PGDS FPBA IC50: 1.0 μM; H-PGDS inhibitor EIA IC50: 0.084 μM.

Provenance & Evidence