Hydrochloric Acid → HCID 178487228, compound

HRID 1749934Notes

Reaction equation

HRID 1749934 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]2[C:7](=[O:24])/[C:8](=[CH:10]/[C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:18]=4)[NH:13][N:12]=3)/[O:9][C:5]=2[C:4]=1[CH2:27][N:28]1[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]1.Cl>C(Cl)Cl.O1CCOCC1>[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]2[C:7](=[O:24])/[C:8](=[CH:10]/[C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([S:20]([CH3:23])(=[O:21])=[O:22])[CH:18]=4)[NH:13][N:12]=3)/[O:9][C:5]=2[C:4]=1[CH2:27][N:28]1[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178487234HCID 178487234, compound

Product 1

HCID 178487228HCID 178487228, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (Z)-4-[(6-methoxy-2-{[5-(methylsulfonyl)-1H-indazol-3-yl]methylene}-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.0462 g, 0.0812 mmol) in methylene chloride (1 mL) was added with a 4 M solution of hydrogen chloride in 1,4-dioxane (1 mL), and the mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated, the resulting residue was added with saturated aqueous sodium hydrogencarbonate, and the mixture was extracted five times with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated to obtain (Z)-6-methoxy-2-{[5-(methylsulfonyl)-1H-indazol-3-yl]methylene}-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one (0.0277 g, 72%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe resulting residue was added with saturated aqueous sodium hydrogencarbonate
  3. extractionthe mixture was extracted five 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-ded2fbf10cd645d0bbd9771322e7a42e
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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