Hydrazine hydrate (1:1) → 1-{[4-Chloro-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-amine

HRID 1946331Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:13]=[CH:12][C:11]([N:14]3C(=O)C4C(=CC=CC=4)C3=O)=[N:10]2)=[C:4]([C:25]([F:28])([F:27])[F:26])[CH:3]=1.O.NN>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:13]=[CH:12][C:11]([NH2:14])=[N:10]2)=[C:4]([C:25]([F:26])([F:28])[F:27])[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of crude 2-(1-{[4-chloro-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-1H-isoindole-1,3(2H)-dione (6.14 g, 15.1 mmol) in THF (50 ml) was added hydrazine hydrate (3.67 ml, 76 mmol, Aldrich). The resulting colourless solution was stirred at 50° C. for 1 h. A white solid precipitated. The reaction was cooled down to ambient temperature and filtered through a sinter funnel. The filtrate was then passed through a hydrophobic frit and concentrated under reduced pressure. The sample was pre-absorbed on florosil (15 ml of DCM:MeOH=1:1) and purified on silica 100 g using 0-50% ethyl acetate-dichloromethane. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a white solid (1.57 g); LCMS: (System 3) MH+=276, tRET=0.90 min.

Workup

customA white solid precipitated
temperatureThe reaction was cooled down to ambient temperature
filtrationfiltered through a sinter funnel
concentrationconcentrated under reduced pressure
customThe sample was pre-absorbed on florosil (15 ml of DCM:MeOH=1:1)
custompurified on silica 100 g
customevaporated in vacuo

Sources & evidence

ORD record: ord-33dfd5763f1245cbabe2498739ce5091
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399436B2

Reaction notes

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