Trifluoroacetic acid → HCID 24954649, compound

HRID 1952169Notes

Reaction equation

HRID 1952169 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([CH:11]([C:13]3[N:14]([CH2:27][CH3:28])[N:15]=[C:16]([NH:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[CH:17]=3)O)=[CH:9][N:8]([Si](C(C)C)(C(C)C)C(C)C)[C:5]2=[N:6][CH:7]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][C:13]3[N:14]([CH2:27][CH3:28])[N:15]=[C:16]([NH:18][CH2:19][C:20]4[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=4)[CH:17]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 66970959HCID 66970959, compound

Product 1

HCID 24954649HCID 24954649, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(5-Chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[2-ethyl-5-(4-fluoro-benzylamino)-2H-pyrazol-3-yl]-methanol (630, 0.045 g, 0.081 mmol) was dissolved in acetonitrile (5 mL) and triethylsilane (0.4 mL, 2.0 mmol) was added, followed by trifluoroacetic acid (0.2 mL, 2.0 mmol). The reaction was stirred at room temperature for 45 minutes, then stirred at 60° C. for 45 minutes. The solvent was removed under reduced pressure, ethyl acetate was added and the organic was washed with sodium bicarbonate saturated solution and brine. After drying over anhydrous sodium sulfate, the solvent was evaporated to dryness. Purification with silica gel column chromatography eluting with a gradient of ethyl acetate (40-100%) in hexanes gave the isolation of the desired compound (P-0185, 0.0068 g, 22%). MS (ESI) [M+H+]+=384.1.

Workup

  1. stirringstirred at 60° C. for 45 minutes
  2. customThe solvent was removed under reduced pressure, ethyl acetate
  3. additionwas added
  4. washthe organic was washed with sodium bicarbonate saturated solution and brine
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe solvent was evaporated to dryness
  7. customPurification with silica gel column chromatography
  8. washeluting with a gradient of ethyl acetate (40-100%) in hexanes

Sources & evidence

ORD record
ord-56829565369841c487b6343ea8c80d83
Source dataset
uspto-grants-2013_03
Patent number
US08404700B2

Reaction notes

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