Dimethylformamide → 4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-3-fluorophenoxy)picolinamide

HRID 520695Notes

Reaction equation

HRID 520695 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([C:12]1[C:13](=[O:25])[N:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:15]([CH3:18])[C:16]=1[CH3:17])=[O:11].CC([O-])(C)C.[K+].CN(C=O)C.Cl[C:38]1[CH:43]=[CH:42][N:41]=[C:40]([C:44]([NH2:46])=[O:45])[CH:39]=1>CCOC(C)=O.O>[CH3:18][N:15]1[C:16]([CH3:17])=[C:12]([C:10]([NH:9][C:3]2[CH:4]=[CH:5][C:6]([O:8][C:38]3[CH:43]=[CH:42][N:41]=[C:40]([C:44]([NH2:46])=[O:45])[CH:39]=3)=[CH:7][C:2]=2[F:1])=[O:11])[C:13](=[O:25])[N:14]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 3035434-Chloropyridine-2-carboxamideHCID 23665647Potassium tert-butoxideHCID 90032748N-(2-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

Product 1

HCID 730510744-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-3-fluorophenoxy)picolinamideYield 91.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of N-(2-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (300 mg, 0.879 mmol) and t-BuOK (118 mg, 1.05 mmol) was added DMF (2.5 mL). The resulted mixture was stirred at rt for 30 minutes, then 4-chloropicolinamide (165 mg, 1.05 mmol) was added. The mixture was heated at 120° C. for 5 hours, then cooled to rt, and H2O (50 mL) and EtOAc (2 mL) was added. The resulted mixture was stirred at rt overnight. Filtered and the precipitation was washed with water (5 mL) to give the title compound as a dark brown solid (370 mg, 91.2%).

Workup

  1. temperatureThe mixture was heated at 120° C. for 5 hours
  2. temperaturecooled to rt
  3. stirringThe resulted mixture was stirred at rt overnight
  4. filtrationFiltered
  5. customthe precipitation
  6. washwas washed with water (5 mL)

Sources & evidence

ORD record
ord-79791acf976e410ca91cf08d39416cb5
Source dataset
uspto-grants-2016_05
Patent number
US09326975B2

Reaction notes

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