Hydrochloric Acid → HCID 178515790, compound

HRID 1749920Notes

Reaction equation

HRID 1749920 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:14](=[CH:17][C:18]4[O:19][CH2:20][O:21][C:22]=4[C:23]=3[CH2:24][N:25]3[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]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:14](=[CH:17][C:18]4[O:19][CH2:20][O:21][C:22]=4[C:23]=3[CH2:24][N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[C:15]\2=[O:16])=[N:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178452289HCID 178452289, compound

Product 1

HCID 178515790HCID 178515790, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({6-[(1H-indazol-3-yl)methylene]-7-oxo-6,7-dihydrobenzofuro[5,6-d][1,3]dioxol-4-yl}methyl)piperazine-1-carboxylate (0.019 g, 0.038 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. The mixture was azeotroped with toluene under reduced pressure to remove the solvent and hydrogen chloride. 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. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (99:1→95:5)) to obtain (Z)-6-[(1H-indazol-3-yl)methylene]-4-(piperazin-1-ylmethyl)benzofuro[5,6-d][1,3]dioxol-7(6H)-one (0.005 g, 33%).

Workup

  1. customThe mixture was azeotroped with toluene under reduced pressure
  2. customto remove the solvent and hydrogen chloride
  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
  8. washthe residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (99:1→95:5))

Sources & evidence

ORD record
ord-9a910b9c7a624ac8b4f819b5edae8296
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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