Hydrochloric Acid → HCID 178515792, compound

HRID 1749908Notes

Reaction equation

HRID 1749908 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]([C:21]([N:23]4[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]4)=[O:22])=[C:19]([OH:36])[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\[O:12][C:13]3[C:20]([C:21]([N:23]4[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]4)=[O:22])=[C:19]([OH:36])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178452356HCID 178452356, compound

Product 1

HCID 178515792HCID 178515792, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (Z)-4-{2-[(1H-indazol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-carbonyl}piperazine-1-carboxylate (0.054 g, 0.11 mmol) in methylene chloride (3.0 mL) was added with a 4 M solution of hydrogen chloride in 1,4-dioxane (3.0 mL), and then the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the mixture was azeotroped twice with toluene under reduced pressure. The residual solid was added with water, and then the mixture was adjusted to pH 9 with saturated aqueous sodium hydrogencarbonate, and the solid was collected by filtration and dried to obtain (Z)-2-[(1H-indazol-3-yl)methylene]-6-hydroxy-7-(piperazine-1-carbonyl)benzofuran-3(2H)-one (0.018 g, 42%).

Workup

  1. customAfter completion of the reaction
  2. customthe mixture was azeotroped twice with toluene under reduced pressure
  3. additionThe residual solid was added with water
  4. filtrationthe solid was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-214787cbe67546ac9830d25f08ccd8a5
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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