Triethylamine → HCID 12115478, compound

HRID 2373329Notes

Reaction equation

HRID 2373329 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[C:12]([OH:14])=O.[CH3:15][CH:16]([C:21]1[CH:27]=[C:26]([CH:28]([C:33]([F:36])([F:35])[F:34])[C:29]([F:32])([F:31])[F:30])[CH:25]=[CH:24][C:22]=1[NH2:23])[CH2:17][CH:18]([CH3:20])[CH3:19].C(N(CC)CC)C>S(Cl)(Cl)=O.O1CCCC1.C(OCC)(=O)C>[CH3:15][CH:16]([C:21]1[CH:27]=[C:26]([CH:28]([C:29]([F:31])([F:32])[F:30])[C:33]([F:34])([F:35])[F:36])[CH:25]=[CH:24][C:22]=1[NH:23][C:12]([C:3]1[C:4]([C:8]([F:11])([F:10])[F:9])=[N:5][N:6]([CH3:7])[C:2]=1[Cl:1])=[O:14])[CH2:17][CH:18]([CH3:19])[CH3:20]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27738065-Chloro-1-Methyl-3-(Trifluoromethyl)-1H-Pyrazole-4-Carboxylic AcidHCID 12115477HCID 12115477, compound

Product 1

HCID 12115478HCID 12115478, compoundYield 43.3%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 24386Thionyl ChlorideSolvent

Procedure

5-Chloro-1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid (230 mg, 1 mmol) was dissolved in thionyl chloride (2 ml), and the solution was stirred at reflux temperature for 2 hours. After concentration under reduced pressure, the resulting acid chloride was added to a solution of 2-(1,3-dimethylbutyl)-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline (330 mg, 1 mmol) and triethylamine (150 mg, 1.5 mmol) in tetrahydrofuran (10 ml) under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and then washed with water. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure, and the resulting residue was separated and purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain 233 mg of the desired compound.

Workup

  1. temperatureat reflux temperature for 2 hours
  2. concentrationAfter concentration under reduced pressure
  3. temperaturecooling
  4. stirringthe resulting mixture was stirred at room temperature for 2 hours
  5. washwashed with water
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe resulting residue was separated
  9. custompurified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-f97285f705ca4013b165a1494cc99cab
Source dataset
uspto-grants-2008_12
Patent number
US07459477B2

Reaction notes

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