Hydrochloric Acid → HCID 86681994, compound

HRID 1749804Notes

Reaction equation

HRID 1749804 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[C:10](/[CH:11]=[C:12]3\[O:13][C:14]4[C:21]([CH2:22][N:23]5[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]5)=[C:20]([OH:36])[CH:19]=[CH:18][C:15]=4[C:16]\3=[O:17])[C:5]2=[CH:4][CH:3]=1.[ClH:37]>C(Cl)Cl.O1CCOCC1>[ClH:1].[ClH:37].[ClH:1].[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[C:10](/[CH:11]=[C:12]3\[O:13][C:14]4[C:21]([CH2:22][N:23]5[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]5)=[C:20]([OH:36])[CH:19]=[CH:18][C:15]=4[C:16]\3=[O:17])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86681993HCID 86681993, compound

Product 1

HCID 86681994HCID 86681994, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.020 g, 0.039 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 a mixed solvent of methylene chloride and diethyl ether and thereby washed to obtain (Z)-2-[(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-hydroxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one trihydrochloride (0.015 g, 75%).

Workup

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

Sources & evidence

ORD record
ord-52a9ecd527d04077bcb6f86e9fe09ad8
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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