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Water → 4-[1-(2-Thiazolylcarbamoyl)-1H-indol-5-yloxy]-6,7-dimethoxyquinoline

HRID 387888
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 387888
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[C:20]4[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=4)[N:14]=[CH:13][CH:12]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[S:27]1[CH:31]=[CH:30][N:29]=[C:28]1[NH:32][C:33](=O)[O:34]C1C=CC=CC=1.O>CN(C)C=O.C(OCC)(=O)C>[S:27]1[CH:31]=[CH:30][N:29]=[C:28]1[NH:32][C:33]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[C:20]4[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=4)[N:14]=[CH:13][CH:12]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)=[O:34]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 651148phenyl N-(1,3-thiazol-2-yl)carbamateHCID 221326454-[(1H-Indol-5-yl)oxy]-6,7-dimethoxyquinoline

Produkt 1

HCID 589313554-[1-(2-Thiazolylcarbamoyl)-1H-indol-5-yloxy]-6,7-dimethoxyquinolineAusbeute 66,04 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

After dissolving 4-(1H-indol-5-yloxy)-6,7-dimethoxyquinoline (25 mg, 0.0780 mmol) in N,N-dimethylformamide (0.4 ml), sodium hydride (6 mg) was added and the mixture was stirred at room temperature for 15 minutes. Phenyl N-(2-thiazolyl)carbamate (30 mg, 0.1362 mmol) was further added and the mixture was stirred at 80° C. for 2 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate, the extract was washed with saturated saline and dried over anhydrous magnesium sulfate, and the filtrate was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate/ethanol system), the obtained crystals were suspended in ethanol and diluted with hexane, and then the crystals were filtered out, washed with hexane and dried by aspiration to obtain the title compound (23 mg, 0.0515 mmol, 66.04%) as light yellow crystals.

Aufarbeitung

  1. additionwas added
  2. stirringthe mixture was stirred at 80° C. for 2 hours
  3. washthe extract was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe filtrate was distilled off under reduced pressure
  6. additiondiluted with hexane
  7. filtrationthe crystals were filtered out
  8. washwashed with hexane
  9. customdried by aspiration

Quellen und Nachweise

ORD-Eintrag
ord-8f1d6982f6844b73b240227f27007105
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08372981B2

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