Dimethylformamide → N-(4-((2-amino-3-chloropyridin-4-yl)oxy)-2-fluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 870462Notes

Reaction equation

HRID 870462 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(N)=O)=[N:35][CH:36]=[CH:37][C:38]=1Cl.CCOC(C)=O.C[N:50](C=O)C>O>[NH2:50][C:34]1[C:33]([Cl:32])=[C:38]([O:8][C:6]2[CH:5]=[CH:4][C:3]([NH:9][C:10]([C:12]3[C:13](=[O:25])[N:14]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:15]([CH3:18])[C:16]=3[CH3:17])=[O:11])=[C:2]([F:1])[CH:7]=2)[CH:37]=[CH:36][N:35]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 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 73053651N-(4-((2-amino-3-chloropyridin-4-yl)oxy)-2-fluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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-8abf65eec024407bb66471477fd7818d
Source dataset
uspto-grants-2015_03
Patent number
US08969388B1

Reaction notes

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