Ethanol → N-{3-Cyano-4-[4-(2-cyano-3-hydroxycrotonoyl)piperazin-1-yl]phenyl}-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamide

HRID 1744594Notes

Reaction equation

HRID 1744594 reaction equation
C(O)C.[C:4]([C:6]1[CH:7]=[C:8]([NH:26][C:27]([C:29]2[CH:30]=[N:31][N:32]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)[C:33]=2[CH3:34])=[O:28])[CH:9]=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([C:18]([C:20]2[CH:21]=[N:22][O:23][C:24]=2[CH3:25])=[O:19])[CH2:14][CH2:13]1)#[N:5].[OH-].[Na+]>O>[C:4]([C:6]1[CH:7]=[C:8]([NH:26][C:27]([C:29]2[CH:30]=[N:31][N:32]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)[C:33]=2[CH3:34])=[O:28])[CH:9]=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([C:18](=[O:19])/[C:20](/[C:21]#[N:22])=[C:24](\[OH:23])/[CH3:25])[CH2:14][CH2:13]1)#[N:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 22228167N-{3-Cyano-4-[4-(5-methylisoxazol-4-ylcarbonyl)piperazin-1-yl]phenyl}-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamide

Product 1

HCID 69648879N-{3-Cyano-4-[4-(2-cyano-3-hydroxycrotonoyl)piperazin-1-yl]phenyl}-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamideYield 47.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixed solvent of ethanol (10 ml) and water (10 ml) containing N-{3-cyano-4-[4-(5-methylisoxazol-4-ylcarbonyl) piperazin-1-yl]phenyl}-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamide (0.95 g) and sodium hydroxide (0.1 g) was stirred at a refluxing temperature for 2 h. The solvent was evaporated under reduced pressure. Dilute hydrochloric acid was added to the residue to allow crystallization. The crystals were recrystallized from hydrous dimethylformamide to give the title compound (0.45 g), melting point: 210° C.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionDilute hydrochloric acid was added to the residue
  3. customcrystallization
  4. customThe crystals were recrystallized from hydrous dimethylformamide

Sources & evidence

ORD record
ord-568dee4af188439a97b694b930c080b6
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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