Trifluoroacetic acid → HCID 178461563, compound

HRID 1749853Notes

Reaction equation

HRID 1749853 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[C:20]([CH2:21][N:22]4[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][C@@H:23]4[CH3:35])=[C:19]([OH:36])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1.FC(F)(F)C(O)=O>C(Cl)Cl.C(=O)([O-])O.[Na+]>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[C:20]([CH2:21][N:22]4[CH2:27][CH2:26][NH:25][CH2:24][C@@H:23]4[CH3:35])=[C:19]([OH:36])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178461581HCID 178461581, compound

Product 1

HCID 178461563HCID 178461563, compoundYield 17.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(1H-indazol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)-3-(S)-methylpiperazine-1-carboxylate (0.329 g, 0.672 mmol) in methylene chloride (8 mL) was added with trifluoroacetic acid (8 mL) at room temperature, and the mixture was stirred overnight. The reaction mixture was concentrated, then the residue was added with methanol (20 mL) and a 5% solution of hydrogen chloride in methanol (5 mL), and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated, and then the residue was suspended in acetonitrile and thereby washed to obtain orange solid. This solid was dissolved in saturated aqueous sodium hydrogencarbonate, and the solution was extracted three times with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate to obtain the objective (Z)-2-[(1H-indazol-3-yl)methylene]-6-hydroxy-7-{[2-(S)-methylpiperazin-1-yl]methyl}benzofuran-3(2H)-one (0.0460 g, 17%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was added with methanol (20 mL)
  3. stirringa 5% solution of hydrogen chloride in methanol (5 mL), and the mixture was stirred at room temperature for 2 hours
  4. customThe solvent was evaporated
  5. washwashed
  6. customto obtain orange solid
  7. extractionthe solution was extracted three times with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-0f8d6a5acac44836b8132e8927b63794
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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