Triethylamine → HCID 12115480, compound

HRID 2373331Notes

Reaction equation

HRID 2373331 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([OH:10])=O)[C:4]([CH3:11])=[N:3]1.[CH3:12][CH:13]([C:18]1[CH:24]=[C:23]([C:25]([O:34][CH3:35])([C:30]([F:33])([F:32])[F:31])[C:26]([F:29])([F:28])[F:27])[CH:22]=[CH:21][C:19]=1[NH2:20])[CH2:14][CH:15]([CH3:17])[CH3:16].C(N(CC)CC)C>S(Cl)(Cl)=O.O1CCCC1.C(OCC)(=O)C>[CH3:12][CH:13]([C:18]1[CH:24]=[C:23]([C:25]([O:34][CH3:35])([C:26]([F:27])([F:28])[F:29])[C:30]([F:31])([F:32])[F:33])[CH:22]=[CH:21][C:19]=1[NH:20][C:8]([C:5]1[C:4]([CH3:11])=[N:3][N:2]([CH3:1])[C:6]=1[CH3:7])=[O:10])[CH2:14][CH:15]([CH3:16])[CH3:17]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 7365141,3,5-trimethyl-1H-pyrazole-4-carboxylic acidHCID 12115479HCID 12115479, compound

Product 1

HCID 12115480HCID 12115480, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 24386Thionyl ChlorideSolvent

Procedure

1,3,5-Trimethylpyrazole-4-carboxylic acid (154 mg, 1 mmol) was dissolved in thionyl chloride (5 ml), and the solution was heated under reflux for 2 hours. The reaction solution was concentrated under reduced pressure, and the resulting acid chloride was added to a solution of 2-(1,3-dimethylbutyl)-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-aniline (345 mg, 1 mmol) and triethylamine (150 mg, 1.5 mmol) in tetrahydrofuran (10 ml) under ice-cooling, after which the resulting mixture was heated under reflux 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 1:2) to obtain 200 mg of the desired compound.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. temperaturecooling
  5. temperatureafter which the resulting mixture was heated
  6. temperatureunder reflux for 2 hours
  7. washwashed with water
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customthe resulting residue was separated
  11. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-b6c3f9bb0a3949b5ae6bd8dd67d58466
Source dataset
uspto-grants-2008_12
Patent number
US07459477B2

Reaction notes

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