Dimethylformamide → 1-(5-trifluoromethylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxamide

HRID 1748541Notes

Reaction equation

HRID 1748541 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([OH:19])=O.C(Cl)(=O)C(Cl)=O.C[N:27](C)C=O.[NH4+].[OH-]>ClCCl.O1CCCC1>[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([NH2:27])=[O:19]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 162278455-methyl-1-(5-(trifluoromethyl)pyridin-2-yl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 471413721-(5-trifluoromethylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid (2.07 g) described in Reference Example 8 in dichloromethane (50 ml) were added oxalyl chloride (2.62 ml) and N,N-dimethylformamide (catalytic amount) at room temperature, stirred at room temperature for 2 hours, and then the solvent and an excess amount of oxalyl chloride were evaporated. To the obtained reaction mixture was added tetrahydrofuran (50 ml), then 28% ammonia aqueous solution (30 ml) was added thereto under ice-cooling, and stirred at room temperature overnight. After completion of the reaction, the organic solvent was evaporated in vacuo, then 1 N aqueous solution of sodium hydroxide was added thereto, the precipitated solid was collected by filtration, and dried at 60° C. under air blow to give the titled compound (1.8 g) as a pale yellow solid. MS (ESI) m/z: 271 (M+H)+.

Workup

  1. customthe solvent and an excess amount of oxalyl chloride were evaporated
  2. customTo the obtained reaction mixture
  3. temperatureunder ice-cooling
  4. stirringstirred at room temperature overnight
  5. customAfter completion of the reaction
  6. customthe organic solvent was evaporated in vacuo
  7. addition1 N aqueous solution of sodium hydroxide was added
  8. filtrationthe precipitated solid was collected by filtration
  9. customdried at 60° C. under air blow

Sources & evidence

ORD record
ord-ef8a91c5500f474287fdb57369c03bf5
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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