Ethyl formate → 5-Fluoro-6-oxo-2-(quinolin-6-ylamino)-1,6-dihydropyridin-3-carbonitrile

HRID 340439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 340439
[CH:1](OCC)=O.[H-].[Na+].C([O:11][CH2:12][CH2:13][F:14])(=O)C.[C:15]([CH2:17][C:18]([NH:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[N:27]=[CH:26][CH:25]=[CH:24]2)=[NH:19])#[N:16]>C(O)C.CCCCCC>[F:14][C:13]1[C:12](=[O:11])[NH:19][C:18]([NH:20][C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[N:27]=[CH:26][CH:25]=[CH:24]3)=[C:17]([C:15]#[N:16])[CH:1]=1

Komponenten

7

Edukt 4

HCID 8025Ethyl formateHCID 10016Ethanol, 2-fluoro-, 1-acetateHCID 24758Sodium hydrideHCID 178511140HCID 178511140, Verbindung

Produkt 1

HCID 686063515-Fluoro-6-oxo-2-(quinolin-6-ylamino)-1,6-dihydropyridin-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

Ethyl formate (16.1 ml) was added to a hexane (40 ml) suspension containing sodium hydride (60% in oil, 2.4 g) at room temperature, and then fluoroethyl acetate (3.86 ml) was added dropwise under ice cooling, followed by stirring at room temperature for 15 minutes. Ethanol (50 ml) was added to the reaction mixture, and then an ethanol (50 ml) solution containing 2-cyano-N-(quinolin-6-yl)acetamidine (4.20 g) was added dropwise, followed by stirring at 80° C. for 2 hours. The reaction mixture was cooled to room temperature. Then, solid matter was collected by filtration and washed with ethyl acetate, and a yellow solid of 5-fluoro-6-oxo-2-(quinolin-6-ylamino)-1,6-dihydropyridin-3-carbonitrile (3.71 g) was thus obtained.

Aufarbeitung

  1. additionwas added dropwise
  2. stirringby stirring at 80° C. for 2 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationThen, solid matter was collected by filtration
  5. washwashed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0af78f720882434f8794c4e806fad912
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895585B2

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