Ethanol → HCID 45275253, compound

HRID 2205832Notes

Reaction equation

HRID 2205832 reaction equation
[CH3:1][N:2]1[C:6]([NH:7]C(=O)C)=[C:5]([C:11]#[C:12][Si](C)(C)C)[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:3]1.C([OH:25])C.[OH-].[Na+]>C(OCC)(=O)C.O>[NH2:7][C:6]1[N:2]([CH3:1])[N:3]=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5]=1[C:11](=[O:25])[CH3:12]

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 86717323HCID 86717323, compound

Product 1

HCID 45275253HCID 45275253, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of N-(1-methyl-3-phenyl-4-((trimethylsilyl)ethynyl)-1H-pyrazol-5-yl)acetamide (2.3 g, 7.4 mmol), ethanol (20 mL) and 25% aq. NaOH solution (20 mL) was heated with stirring at 90° C. for 6 h and cooled to room temperature. The reaction mixture was diluted with ethyl acetate and water. The organic phase was washed with water and brine, dried (phase separator cartridge) and concentrated in vacuo. The residue was purified using chromatography (silica gel, gradient 0 to 40% ethyl acetate/CH2Cl2), followed by trituration in diethyl ether to provide the title compound as a white solid (724 mg).

Workup

  1. temperaturewas heated
  2. temperaturecooled to room temperature
  3. washThe organic phase was washed with water and brine
  4. customdried (phase separator cartridge)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-6de3c3fcf66e4259a4b642a8aad1ed7d
Source dataset
uspto-grants-2016_06
Patent number
US09371332B2

Reaction notes

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