Hydrochloric Acid → HCID 86681991, compound

HRID 1749796Notes

Reaction equation

HRID 1749796 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)=[C:19]([OH:35])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1.[ClH:36]>C(Cl)Cl.O1CCOCC1>[ClH:36].[ClH:36].[ClH:36].[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[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]4)=[C:19]([OH:35])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86681990HCID 86681990, compound

Product 1

HCID 86681991HCID 86681991, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.0788 g, 0.165 mmol) in methylene chloride (2 mL) was added with a 4 M solution of hydrochloric acid in dioxane (2 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered, and the resulting solid was washed with acetonitrile to obtain the objective (Z)-2-[(1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-hydroxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one trihydrochloride (0.0518 g, 64%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe resulting solid was washed with acetonitrile

Sources & evidence

ORD record
ord-034f30b79f6c452e8dd07bf0b2296a7b
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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