Dimethylformamide → HCID 22227869, compound

HRID 1744595Notes

Reaction equation

HRID 1744595 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:16][C:17]([C:19]2[CH:20]=[N:21][N:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:23]=2[CH3:24])=[O:18])[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)#[N:2].C(=O)([O-])[O-].[K+].[K+].[C:38](OCCBr)(=[O:40])[CH3:39].CN(C)C=O>O>[C:1]([C:3]1[CH:4]=[C:5]([NH:16][C:17]([C:19]2[CH:20]=[N:21][N:22]([C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[C:23]=2[CH3:24])=[O:18])[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:15][CH2:14][CH2:13][N:12]([CH2:39][CH2:38][OH:40])[CH2:11][CH2:10]1)#[N:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 22228039HCID 22228039, compound

Product 1

HCID 22227869HCID 22227869, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

N-[3-Cyano-4-(homopiperazin-1-yl)phenyl]-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamide (1.5 g), potassium carbonate (0.6 g) and 2-bromoethyl acetate (0.7 g) were added to dimethylformamide (20 ml) and the mixture was stirred at 60° C. for 1 h. The reaction mixture was added into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated under reduced pressure. To the residue were added 2N aqueous sodium hydroxide solution (10 ml) and ethanol (20 ml) and the mixture was stirred at a refluxing temperature for 1 h. The solvent was evaporated under reduced pressure and dilute hydrochloric acid was added. The obtained crystals were recrystallized from hydrous ethanol to give the title compound (1.1 g), melting point: 124° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customthe solvent was evaporated under reduced pressure
  4. additionTo the residue were added 2N aqueous sodium hydroxide solution (10 ml) and ethanol (20 ml)
  5. stirringthe mixture was stirred at a refluxing temperature for 1 h
  6. customThe solvent was evaporated under reduced pressure and dilute hydrochloric acid
  7. additionwas added
  8. customThe obtained crystals were recrystallized from hydrous ethanol

Sources & evidence

ORD record
ord-75ff10feab0541b68cfc329e3b2cfee0
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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