Hydrochloric Acid → (2Z)-2-(2H-indazol-3-ylmethylidene)-5,6-dimethoxy-7-(piperazin-1-ylmethyl)-1-benzofuran-3-one

HRID 1749915Notes

Reaction equation

HRID 1749915 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])[C:18]([O:37][CH3:38])=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1.Cl>C(Cl)Cl.O1CCOCC1>[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])[C:18]([O:37][CH3:38])=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178486622HCID 178486622, compound

Product 1

HCID 178486621(2Z)-2-(2H-indazol-3-ylmethylidene)-5,6-dimethoxy-7-(piperazin-1-ylmethyl)-1-benzofuran-3-oneYield 76.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(1H-indazol-3-yl)methylene]-5,6-dimethoxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.026 g, 0.050 mmol) in methylene chloride (2.0 mL) was added with a 4 M solution of hydrogen chloride in 1,4-dioxane (2.0 mL), and then the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the mixture was azeotroped twice with toluene under reduced pressure. The residual solid was added with water, and then the mixture was adjusted to pH 9 with saturated aqueous sodium hydrogencarbonate, and extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure to obtain (Z)-2-[(1H-indazol-3-yl)methylene]-5,6-dimethoxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one (0.016 g, 76%).

Workup

  1. customAfter completion of the reaction
  2. customthe mixture was azeotroped twice with toluene under reduced pressure
  3. additionThe residual solid was added with water
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-73485d354c4248fb9728d66276ce1d6f
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

Loading…