Hydrazine hydrate (1:1) → 3-amino-5-sec-butyl-7-(1-methyl-1H-pyrazol-3-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one

HRID 1526379Notes

Reaction equation

[CH:1]([N:5]1[CH:10]=[C:9]([C:11]2[CH:15]=[CH:14][N:13]([CH3:16])[N:12]=2)[C:8](OC)=[C:7]([C:19]#[N:20])[C:6]1=[O:21])([CH2:3][CH3:4])[CH3:2].O.[NH2:23][NH2:24]>C(O)C>[NH2:20][C:19]1[C:7]2[C:6](=[O:21])[N:5]([CH:1]([CH2:3][CH3:4])[CH3:2])[CH:10]=[C:9]([C:11]3[CH:15]=[CH:14][N:13]([CH3:16])[N:12]=3)[C:8]=2[NH:24][N:23]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 1-(sec-butyl)-4-methoxy-5-(1-methyl-1H-pyrazol-3-yl)-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step C (140 mg) and ethanol (5 mL) was added hydrazine monohydrate (122 mg), and the mixture was stirred at 90° C. for 1 hr, cooled to room temperature, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane), and recrystallized from ethyl acetate/diisopropyl ether to give the title compound (82 mg).

Workup

temperaturecooled to room temperature
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane)
customrecrystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record: ord-6426d8159437455fa3fcfc5e51c69cb4
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085578B2

Reaction notes

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