Hydrochloric Acid → HCID 178487227, compound

HRID 1749930Notes

Reaction equation

HRID 1749930 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]2[C:7](=[O:29])/[C:8](=[CH:10]/[C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][CH2:22][N:23]5[CH2:28][CH2:27][O:26][CH2:25][CH2:24]5)[CH:18]=4)[NH:13][N:12]=3)/[O:9][C:5]=2[C:4]=1[CH2:32][N:33]1[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]1.Cl>C(Cl)Cl.O1CCOCC1>[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]2[C:7](=[O:29])/[C:8](=[CH:10]/[C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][CH2:22][N:23]5[CH2:24][CH2:25][O:26][CH2:27][CH2:28]5)[CH:18]=4)[NH:13][N:12]=3)/[O:9][C:5]=2[C:4]=1[CH2:32][N:33]1[CH2:34][CH2:35][NH:36][CH2:37][CH2:38]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178487233tert-butyl 4-[[(2Z)-6-methoxy-2-[[5-(2-morpholin-4-ylethoxy)-2H-indazol-3-yl]methylidene]-3-oxo-1-benzofuran-7-yl]methyl]piperazine-1-carboxylate

Product 1

HCID 178487227HCID 178487227, compoundYield 56.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (Z)-4-[(6-methoxy-2-{[5-(2-morpholinoethoxy)-1H-indazol-3-yl]methylene}-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.0273 g, 0.0441 mmol) in methylene chloride (2 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 12 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 washed with saturated brine, and dried over anhydrous sodium sulfate, and then the solvent was evaporated to obtain (Z)-6-methoxy-2-{[5-(2-morpholinoethoxy)-1H-indazol-3-yl]methylene}-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one (0.0130 g, 56%).

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. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0ec974ff096b4b9fabee70685b7c13f3
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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