3-Aminopyridine → 1-methyl-N-(3-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide

HRID 237411Notes

Reaction equation

HRID 237411 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7](O)=[O:8])[C:4]([C:10]([F:13])([F:12])[F:11])=[N:3]1.[NH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1>CN(C=O)C>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([NH:14][C:7]([C:5]2[C:4]([C:10]([F:13])([F:12])[F:11])=[N:3][N:2]([CH3:1])[CH:6]=2)=[O:8])[CH:16]=1

Participants

4

Reactant 2

HCID 100093-AminopyridineHCID 27756651-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 14745791-methyl-N-(3-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamideYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.5 g (12.9 mmol) of 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid in 25 mL of N,N-dimethylformanid (DMF) and 2.1 g (12.9 mmol) of N,N′-carbonyl diimidazole (CDI) were stirred at ambient temperature for 1 hour prior to addition of 1.2 g (12.9 mmol) of 3-aminopyridine. After three days of stirring the solvent was evaporated, the residue dissolved in dichloromethane, washed twice with a saturated solution of NaHCO3 and water. The combined organic phases were evaporated and the crude product was purified by flash column chromatography (silica using dichloromethane/methanol=95/5) to give 1.33 g (48%) of the title compound.

Workup

  1. customwas evaporated
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed twice with a saturated solution of NaHCO3 and water
  4. customThe combined organic phases were evaporated
  5. customthe crude product was purified by flash column chromatography (silica using dichloromethane/methanol=95/5)

Sources & evidence

ORD record
ord-d5ac132f087749a0b8fbd3700bad8c63
Source dataset
uspto-grants-2014_02
Patent number
US08642597B2

Reaction notes

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