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

HRID 520696Notes

Reaction equation

HRID 520696 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+].[Cl:32][C:33]1[C:34]([C:40]([NH2:42])=[O:41])=[N:35][CH:36]=[CH:37][C:38]=1Cl.CCOC(C)=O>CN(C=O)C.O>[Cl:32][C:33]1[C:34]([C:40]([NH2:42])=[O:41])=[N:35][CH:36]=[CH:37][C:38]=1[O:8][C:6]1[CH:5]=[CH:4][C:3]([NH:9][C:10]([C:12]2[C:13](=[O:25])[N:14]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:15]([CH3:18])[C:16]=2[CH3:17])=[O:11])=[C:2]([F:1])[CH:7]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 231651433,4-Dichloropyridine-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 730510753-chloro-4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-3-fluorophenoxy)picolinamideYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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) in DMF (3 mL) was stirred at rt for 30 minutes, then 3,4-dichloropicolinamide (201 mg, 1.05 mmol) was added. The reaction mixture was heated to 120° C. and stirred for 12 hours. EtOAc (1 mL) and H2O (20 mL) were added, and the resulted mixture was stirred at rt overnight. Filtered to give the title compound as a brown solid (379 mg, 87.0%).

Workup

  1. temperatureThe reaction mixture was heated to 120° C.
  2. stirringstirred for 12 hours
  3. stirringthe resulted mixture was stirred at rt overnight
  4. filtrationFiltered

Sources & evidence

ORD record
ord-783fe0f1f9b547739bf178b84e9cafb8
Source dataset
uspto-grants-2016_05
Patent number
US09326975B2

Reaction notes

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