Hydrochloric Acid → (Z)-2-[(6-ethynyl-1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-hydroxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one trihydrochloride

HRID 1749822Notes

Reaction equation

HRID 1749822 reaction equation
[C:1]([C:3]1[N:8]=[C:7]2[NH:9][CH:10]=[C:11](/[CH:12]=[C:13]3\[O:14][C:15]4[C:22]([CH2:23][N:24]5[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]5)=[C:21]([OH:37])[CH:20]=[CH:19][C:16]=4[C:17]\3=[O:18])[C:6]2=[CH:5][CH:4]=1)#[CH:2].[ClH:38]>C(Cl)Cl.O1CCOCC1>[ClH:38].[ClH:38].[ClH:38].[C:1]([C:3]1[N:8]=[C:7]2[NH:9][CH:10]=[C:11](/[CH:12]=[C:13]3\[O:14][C:15]4[C:22]([CH2:23][N:24]5[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]5)=[C:21]([OH:37])[CH:20]=[CH:19][C:16]=4[C:17]\3=[O:18])[C:6]2=[CH:5][CH:4]=1)#[CH:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86682005tert-butyl (Z)-4-({2-[(6-ethynyl-1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate

Product 1

HCID 86682006(Z)-2-[(6-ethynyl-1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-hydroxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one trihydrochlorideYield 78%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(6-ethynyl-1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.015 g, 0.030 mmol) in methylene chloride (2.0 mL) was added with a 4 M solution of hydrogen chloride in 1,4-dioxane (2.0 mL), and then the mixture was stirred at room temperature for 2 hours. The mixture was azeotroped twice with toluene under reduced pressure, and then the residual solid was suspended in methylene chloride and thereby washed to obtain (Z)-2-[(6-ethynyl-1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-hydroxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one trihydrochloride (0.012 g, 78%).

Workup

  1. customThe mixture was azeotroped twice with toluene under reduced pressure
  2. washwashed

Sources & evidence

ORD record
ord-f49ab8e75ec14ab881aa6efe6f7e5efd
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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