Trifluoroacetic acid → HCID 178487226, compound

HRID 1749884Notes

Reaction equation

HRID 1749884 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2/[CH:11]=[C:12]1\[O:13][C:14]2[C:21]([CH2:22][N:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]3)=[C:20]([O:36][CH3:37])[CH:19]=[CH:18][C:15]=2[C:16]\1=[O:17].FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2/[CH:11]=[C:12]1\[O:13][C:14]2[C:21]([CH2:22][N:23]3[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]3)=[C:20]([O:36][CH3:37])[CH:19]=[CH:18][C:15]=2[C:16]\1=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178487232HCID 178487232, compound

Product 1

HCID 178487226HCID 178487226, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(5-chloro-1H-indazol-3-yl)methylene]-6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.0330 g, 0.0629 mmol) in methylene chloride (2 mL) was added with trifluoroacetic acid (2 mL) at room temperature, and the mixture was stirred overnight. The reaction mixture was concentrated, then the residue was added with saturated aqueous sodium hydrogencarbonate (10 mL), and the mixture was extracted three times with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated to obtain (Z)-2-[(5-chloro-1H-indazol-3-yl)methylene]-6-methoxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one (0.0120 g, 44%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was added with saturated aqueous sodium hydrogencarbonate (10 mL)
  3. extractionthe mixture was extracted three times with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6fbc1d6b8a914b89b59fabdd13aa94aa
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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