Trifluoroacetic acid → HCID 69002178, compound

HRID 1821359Notes

Reaction equation

HRID 1821359 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1/[CH:14]=[CH:15]/[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18](C2CCCCO2)[N:17]=1.FC(F)(F)C(O)=O.[OH-].[Na+]>CO>[NH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16](/[CH:15]=[CH:14]/[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:17]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 68998017HCID 68998017, compound

Product 1

HCID 69002178HCID 69002178, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (E)-3-{2-[2-(2-pyridylamino)phenyl]vinyl}-1-(tetrahydropyran-2-yl)-1H-indazole (49 mg, 1.2 mmol) obtained in Step 2 and trifluoroacetic acid (1.0 mL) in methanol (0.50 mL) was stirred at room temperature for 18 hours. A 2 mol/L aqueous sodium hydroxide solution was added to neutralize the mixture and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=97/3) to obtain Compound 164 (10 mg, 50%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=97/3)

Sources & evidence

ORD record
ord-38c3220ab458425fa17280b0840c70dc
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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