Trifluoroacetic acid → HCID 61632462, compound

HRID 1477586Notes

Reaction equation

HRID 1477586 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:7]=[CH:6][N:5]([CH:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[N:4]=1.FC(F)(F)C(O)=O>ClCCl>[F:22][C:2]([F:1])([F:21])[C:3]1[CH:7]=[CH:6][N:5]([CH:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[N:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 712265361-Piperidinecarboxylic acid, 4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-, 1,1-dimethylethyl ester

Product 1

HCID 61632462HCID 61632462, compoundYield 127.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (1.5 mL) of tert-butyl 4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]piperidine-1-carboxylate (150 mg, 0.50 mmol) synthesized in Reference Synthesis Example 33, trifluoroacetic acid (0.7 mL) was added at room temperature, and the resultant solution was stirred for 3 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure and water was added to the concentrated reaction solution, followed by extraction from the resultant mixture with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (140 mg, quantitative).

Workup

  1. additionwas added at room temperature
  2. customAfter completion of the reaction
  3. concentrationthe reaction solution was concentrated under reduced pressure and water
  4. additionwas added to the concentrated reaction solution
  5. extractionfollowed by extraction from the resultant mixture with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-94a0f81f217243a6bf86df6525b05066
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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