Trifluoroacetic acid → HCID 86623733, compound

HRID 1173418Notes

Reaction equation

HRID 1173418 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:27][C:28]([F:31])([F:30])[F:29])[CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19]C(=O)OC(C)(C)C)=[CH:15][CH:14]=2)=[CH:5][C:4]=1[C:32]([F:35])([F:34])[F:33])#[N:2].[SiH](CC)(CC)CC.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:11][CH2:10][N:9]([CH2:27][C:28]([F:29])([F:30])[F:31])[C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([C:32]([F:33])([F:34])[F:35])[CH:5]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 11677782HCID 11677782, compound

Product 1

HCID 86623733HCID 86623733, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl [4-({2-[[4-cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]ethyl}oxy)phenyl]carbamate (0.132 g, 0.262 mmol; Example 27B) in CH2Cl2 (5 mL) at rt was added Et3SiH (0.10 mL, 0.66 mmol), followed by TFA (2 mL). The mixture was stirred 40 min and slowly poured into satd NaHCO3. The whole was extracted with EtOAc (×3). Combined organics were washed (water, brine), dried over Na2SO4, filtered and concentrated in vacuo, yielding 0.098 g of the title compound as a colorless gum which was used without further purification: MS (APCI) m/z 404 (M+1).

Workup

  1. extractionThe whole was extracted with EtOAc (×3)
  2. washCombined organics were washed (water, brine)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-072aa0e4bf1b49bab495e6c88203f623
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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