Trifluoroacetic acid → N-[5-methyl-6-(4-oxocyclohex-1-en-1-yl)pyridin-3-yl]-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxamide

HRID 1748646Notes

Reaction equation

HRID 1748646 reaction equation
O1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[N:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[CH:21]=[N:22][N:23]([C:26]5[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=5)[C:24]=4C)=[O:19])=[CH:13][C:12]=3[CH3:36])=[CH:7][CH2:6]2)[O:4]CC1.FC(F)(F)C(O)=O>O>[CH3:36][C:12]1[CH:13]=[C:14]([NH:17][C:18]([C:20]2[CH:21]=[N:22][N:23]([C:26]3[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:31]=3)[CH:24]=2)=[O:19])[CH:15]=[N:16][C:11]=1[C:8]1[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86692585N-[6-(1,4-dioxaspiro[4.5]decan-7-en-8-yl)-5-methylpyridin-3-yl]-5-methyl-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxamide

Product 1

HCID 86692586N-[5-methyl-6-(4-oxocyclohex-1-en-1-yl)pyridin-3-yl]-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxamideYield 28.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

N-[6-(1,4-dioxaspiro[4.5]decan-7-en-8-yl)-5-methylpyridin-3-yl]-5-methyl-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxamide (823 mg), trifluoroacetic acid (9 ml) and water (catalytic amounts) was stirred at room temperature overnight. After the reaction, water was added, extracted with chloroform, the aqueous layer was neutralized under cooling by the addition of a saturated aqueous solution of sodium bicarbonate and extracted with chloroform. The organic layer was washed with water and saturated brine respectively and dried over anhydrous sodium sulfate. The solvent was evaporated and the resulting residue was purified with a silica gel column chromatography (chloroform/methanol), washed with ethanol and the resulting solid was dried at 60° C. in vacuo to give N-[5-methyl-6-(4-oxocyclohex-1-en-1-yl)pyridin-3-yl]-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxamide (210 mg) as a white solid.

Workup

  1. additionwas added
  2. extractionextracted with chloroform
  3. temperatureunder cooling by the addition of a saturated aqueous solution of sodium bicarbonate
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with water and saturated brine respectively
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customthe resulting residue was purified with a silica gel column chromatography (chloroform/methanol)
  9. washwashed with ethanol
  10. customthe resulting solid was dried at 60° C. in vacuo

Sources & evidence

ORD record
ord-6df7fe42be9c44a6abb1c2d8589c6ca9
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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