Trifluoroacetic acid → HCID 178487225, compound

HRID 1749883Notes

Reaction equation

HRID 1749883 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][CH2:23]4)=[C:19]([O:35][CH3:36])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1.FC(F)(F)C(O)=O>C(Cl)Cl>[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[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]4)=[C:19]([O:35][CH3:36])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178487231HCID 178487231, compound

Product 1

HCID 178487225HCID 178487225, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(1H-indazol-3-yl)methylene]-6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.188 g, 0.383 mmol) in methylene chloride (6 mL) was added with trifluoroacetic acid (6 mL) at room temperature, and the mixture was stirred overnight. The solvent was evaporated, then the residue was dissolved in methanol (8 mL), the solution was added with a 5% solution of hydrochloric acid in methanol (2 mL), and the mixture was stirred at room temperature for 2 hours. The precipitated solid was collected by filtration, and added to saturated aqueous sodium hydrogencarbonate, and the mixture was extracted three times with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated to obtain the objective (Z)-2-[(1H-indazol-3-yl)methylene]-6-methoxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one (0.0130 g, 8%).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in methanol (8 mL)
  3. additionthe solution was added with a 5% solution of hydrochloric acid in methanol (2 mL)
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. filtrationThe precipitated solid was collected by filtration
  6. additionadded to saturated aqueous sodium hydrogencarbonate
  7. extractionthe mixture was extracted three times with ethyl acetate
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ce59ab37e9de4f7da2405f8bd0a6afc5
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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