Hydrochloric Acid → HCID 178487108, compound

HRID 1749972Notes

Reaction equation

HRID 1749972 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](/[CH:21]=[CH:22]\[CH:23]4[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]4)=[C:19]([O:36][CH3:37])[CH:18]=[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[C:15](=[O:16])[C:14]3[CH:17]=[CH:18][C:19]([O:36][CH3:37])=[C:20](/[CH:21]=[CH:22]\[CH:23]4[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]4)[C:13]=3[O:12]2)=[N:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178487113HCID 178487113, compound

Product 1

HCID 178487108HCID 178487108, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 4-((Z)-2-{(Z)-2-[(1H-indazol-3-yl)methylene]-6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl}vinyl)piperidine-1-carboxylate (0.0387 g, 0.0771 mmol) in methylene chloride (2 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, and then the solvent was evaporated. The resulting residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol) to obtain (Z)-2-[(1H-indazol-3-yl-methylene]-6-methoxy-7-[(Z)-2-(piperidin-4-yl)vinyl]benzofuran-3(2H)-one (0.0108 g, 35%).

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. washThe resulting residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol)

Sources & evidence

ORD record
ord-88beba5fcfa2453fa08aa31b92e751ab
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

Loading…