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Hydrochloric Acid → methyl (Z)-3-{[6-hydroxy-3-oxo-7-(piperazin-1-ylmethyl)benzofuran-2(3H)-ylidene]methyl}-1H-indole-6-carboxylate

HRID 1749747
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1749747
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[C:23]3[O:22]/[C:21](=[CH:24]\[C:25]4[C:33]5[C:28](=[CH:29][C:30]([C:34]([O:36][CH3:37])=[O:35])=[CH:31][CH:32]=5)[NH:27][CH:26]=4)/[C:20](=[O:38])[C:19]=3[CH:18]=[CH:17][C:16]=2[OH:39])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(Cl)Cl.O1CCOCC1>[OH:39][C:16]1[CH:17]=[CH:18][C:19]2[C:20](=[O:38])/[C:21](=[CH:24]/[C:25]3[C:33]4[C:28](=[CH:29][C:30]([C:34]([O:36][CH3:37])=[O:35])=[CH:31][CH:32]=4)[NH:27][CH:26]=3)/[O:22][C:23]=2[C:15]=1[CH2:14][N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 86681942methyl (Z)-3-[(7-{[4-(tert-butoxycarbonyl)piperazin-1-yl]methyl}-6-hydroxy-3-oxobenzofuran-2(3H)-ylidene)methyl]-1H-indole-6-carboxylate

Produkt 1

HCID 71278517methyl (Z)-3-{[6-hydroxy-3-oxo-7-(piperazin-1-ylmethyl)benzofuran-2(3H)-ylidene]methyl}-1H-indole-6-carboxylateAusbeute 43,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344Dichloromethane
Lösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of methyl (Z)-3-[(7-{[4-(tert-butoxycarbonyl)piperazin-1-yl]methyl}-6-hydroxy-3-oxobenzofuran-2(3H)-ylidene)methyl]-1H-indole-6-carboxylate (0.020 g, 0.037 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 solvent was evaporated under reduced pressure, then the residue was added with an excessive amount of triethylamine, and the mixture was azeotroped with toluene. The resulting residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10)) to obtain methyl (Z)-3-{[6-hydroxy-3-oxo-7-(piperazin-1-ylmethyl)benzofuran-2(3H)-ylidene]methyl}-1H-indole-6-carboxylate (0.007 g, 43%).

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was added with an excessive amount of triethylamine
  3. customthe mixture was azeotroped with toluene
  4. washThe resulting residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10))

Quellen und Nachweise

ORD-Eintrag
ord-6fd01017f2904cd7ab1c72cd445a857e
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09156827B2

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