Sodium Acetate → ethyl 1-[2-oxo-2-({2-oxo-2-[3-(trifluoromethyl)phenyl]ethyl}amino)ethyl]-1H-pyrazole-4-carboxylate

HRID 1257427Notes

Reaction equation

HRID 1257427 reaction equation
Cl[C:2](=[O:14])[CH2:3][N:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[N:5]1.[NH2:15][CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1)=[O:18].C([O-])(=O)C.[Na+]>ClCCl.O>[O:14]=[C:2]([NH:15][CH2:16][C:17](=[O:18])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:27])([F:28])[F:26])[CH:20]=1)[CH2:3][N:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[N:5]1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 133658842-Amino-1-[3-(trifluoromethyl)phenyl]ethanoneHCID 58127969HCID 58127969, compound

Product 1

HCID 58127653ethyl 1-[2-oxo-2-({2-oxo-2-[3-(trifluoromethyl)phenyl]ethyl}amino)ethyl]-1H-pyrazole-4-carboxylateYield 16.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The compound (3.2 g) obtained in Example 115c and 2-amino-1-[3-(trifluoromethyl)phenyl]ethanone (2.88 g) were dissolved in dichloromethane (120 mL) and water (40 ml), and an aqueous solution (40 mL) of sodium acetate (2.46 g) was added dropwise under cooling in an ice bath. The reaction mixture was stirred at room temperature overnight, and the organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: petroleum ether-ethyl acetate) to give the title compound (0.92 g) as a colorless solid.

Workup

  1. temperatureunder cooling in an ice bath
  2. customthe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (carrier: silica gel, eluent: petroleum ether-ethyl acetate)

Sources & evidence

ORD record
ord-486c954e01534f8f976f98530fd0fe90
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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