Hydrazine → 5-[4-(1H-Pyrazol-1-yl)benzyl]-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one

HRID 242002Notes

Reaction equation

[N:1]1([C:6]2[CH:28]=[CH:27][C:9]([CH2:10][N:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14](=S)[C:13]([C:22]([O:24]CC)=O)=[N:12]3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[NH2:29][NH2:30]>C(O)C>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH2:10][N:11]3[C:20]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[C:14]4=[N:29][NH:30][C:22](=[O:24])[C:13]4=[N:12]3)=[CH:27][CH:28]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

Conditions

Temperature: 70 °C

Procedure

Ethyl 1-[4-(1H-pyrazol-1-yl)benzyl]-4-thioxo-1,4-dihydrocinnoline-3-carboxylate [(Example 31, Step 4) 449 mg, 1.15 mmol] was dissolved in ethanol (12.0 mL) and treated with hydrazine (0.61 mL, 19.57 mmol, 17 equiv). The mixture was stirred at 70° C. for 30 minutes then cooled to ambient temperature and concentrated in vacuo. The residue was suspended in ethyl acetate and filtered. The resulting solid was washed with dichloromethane and dried under in vacuo to afford the titled compound as a dark red powder.

Workup

temperaturethen cooled to ambient temperature
concentrationconcentrated in vacuo
filtrationfiltered
washThe resulting solid was washed with dichloromethane
customdried under in vacuo

Sources & evidence

ORD record: ord-22ac86e56d6c49678d96d9a6b007a3fa
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653079B2

Reaction notes

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