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Water → 4-(4-Amino-3-fluoro-phenoxy)-7-[(2R)-oxiran-2-yl]methoxyquinoline-6-carbonitrile

HRID 387954
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 387954
CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[NH2:12][C:13]1[CH:32]=[CH:31][C:16]([O:17][C:18]2[C:27]3[C:22](=[CH:23][C:24]([OH:30])=[C:25]([C:28]#[N:29])[CH:26]=3)[N:21]=[CH:20][CH:19]=2)=[CH:15][C:14]=1[F:33].O.[C:35]([O:38][CH2:39][CH3:40])(=O)C>>[NH2:12][C:13]1[CH:32]=[CH:31][C:16]([O:17][C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:30][CH2:40][C@H:39]4[CH2:35][O:38]4)=[C:25]([C:28]#[N:29])[CH:26]=3)[N:21]=[CH:20][CH:19]=2)=[CH:15][C:14]=1[F:33]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1358293794-(4-Amino-3-fluorophenoxy)-6-cyano-7-hydroxyquinoline

Produkt 1

HCID 865914714-(4-Amino-3-fluoro-phenoxy)-7-[(2R)-oxiran-2-yl]methoxyquinoline-6-carbonitrile

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

After adding dimethylformamide (8 ml), p-toluenesulfonic acid (2R)-glycidyl ester (1000 mg) and potassium carbonate (940 mg) to 4-(4-amino-3-fluorophenoxy)-6-cyano-7-hydroxyquinoline (1000 mg), the mixture was heated at 50° C. for 4 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate, and then the organic layer was washed with water and saturated saline in that order and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound (659 mg) as light yellow crystals.

Aufarbeitung

  1. washthe organic layer was washed with water and saturated saline in that order
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe obtained crude product
  5. customwas purified by silica gel column chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d0241d236eee45dfa63924a8bc2863d9
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08372981B2

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