Hydrochloric Acid → HCID 178515798, compound

HRID 1750019Notes

Reaction equation

HRID 1750019 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]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)=[CH:19][CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1.Cl>C(Cl)Cl.O1CCOCC1>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]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][CH2:23]4)=[CH:19][CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178452294HCID 178452294, compound

Product 1

HCID 178515798HCID 178515798, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(1H-pyrazolo[3,4-b]pyridin-3-yl)methylene]-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.0292 g, 0.0633 mmol) in methylene chloride (3 mL) was added with a 4 M solution of hydrogen chloride in 1,4-dioxane (2 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated, the resulting residue was added with saturated aqueous sodium hydrogencarbonate, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (aminopropyl silica was used, chloroform/methanol) to obtain (Z)-2-[(1H-pyrazolo[3,4-b]pyridin-3-yl)methylene]-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one (0.0132 g, 58%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe resulting residue was added with saturated aqueous sodium hydrogencarbonate
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography (aminopropyl silica was used, chloroform/methanol)

Sources & evidence

ORD record
ord-53455ac4745b4d888915624180b061f8
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

Loading…