Benzoylhydrazine → HCID 178420151, compound

HRID 42307

Reaction equation

[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]([NH:23][NH2:24])(=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC1C=CC=CC=1C.ClCCl.CO>[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[NH:14][C:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[N:23][N:24]=3)=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 200 °C

Procedure

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.

Workup

temperatureAfter cooling to room temperature
temperaturethe reaction mixture was heated to 200° C. in an open vessel under a stream of nitrogen for six hours
custompurified by flash silica column chromatography
washElution through a 40-g Analogix® flash silica cartridge with 100% dichloromethane to 2% methanol in dichloromethane

Sources & evidence

ORD record: ord-338fc9d28ac9419f8cc1bbb3448e928e
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536185B2

Linked notes

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