Hydrazine → HCID 178434685, compound

HRID 1671349Notes

Reaction equation

HRID 1671349 reaction equation
C([O:8][C:9](=O)[CH:10]([N:14]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[N:15]1)[C:11](=O)[CH3:12])C1C=CC=CC=1.[NH2:24][NH2:25].[Cl-].[NH4+]>CCO>[CH3:12][C:11]1[C:10]([N:14]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[N:15]2)=[C:9]([OH:8])[NH:24][N:25]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 25517Ammonium ChlorideHCID 672131393-Oxo-2-(3-trifluoromethyl-pyrazol-1-yl)-butyric acid benzyl ester

Product 1

HCID 178434685HCID 178434685, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Oxo-2-(3-trifluoromethyl-pyrazol-1-yl)-butyric acid benzyl ester (800 mg, 2.452 mmol), EtOH (12.30 ml) and hydrazine (0.231 ml, 7.36 mmol) are stirred at 50° C. for hour. The volatiles are removed in vacuo yielding a wet solid which is added to ammonium chloride (sat. aq. 100 ml) and the product is extracted into EtOAc (2×100 ml). The combined organic extracts are washed with brine, dried over Na2SO4, and concentrated in vacuo to give a pale yellow solid. The crude product is purified by ISCO combiflash chromatography, eluting with 0 to 100% (EtOAc/Iso-hexane) on a 24 g SiO2-column to afford the title compound as an orange oil; MS: m/z 233.09 [M+H]+.

Workup

  1. customThe volatiles are removed in vacuo
  2. customyielding a wet solid which
  3. extractionthe product is extracted into EtOAc (2×100 ml)
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto give a pale yellow solid
  8. customThe crude product is purified by ISCO combiflash chromatography
  9. washeluting with 0 to 100% (EtOAc/Iso-hexane) on a 24 g SiO2-column

Sources & evidence

ORD record
ord-52b69926299e40a28a81ab557afb690d
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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