Potassium Carbonate → HCID 59272909, Verbindung

HRID 1400202

Reaktionsgleichung

Reaktionsgleichung von HRID 1400202
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][NH:6][C:5](=[O:9])[C:4]=1[C:10]#[N:11].[CH:12]1([CH2:15][CH2:16]OS(C)(=O)=O)[CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:12]1([CH2:15][CH2:16][N:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([C:10]#[N:11])[C:5]2=[O:9])[CH2:14][CH2:13]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 27867023-Pyridinecarbonitrile, 1,2-dihydro-4-methoxy-2-oxo-HCID 145578092-Cyclopropylethyl methanesulfonate

Produkt 1

HCID 59272909HCID 59272909, VerbindungAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

To a solution of 4-methoxy-2-oxo-1,2-dihydro-pyridine-3-carbonitrile (19.81 g, 131.98 mmol) in acetonitrile (520 ml) were added intermediate 1 (34.36 g, 171.57 mmol) and potassium carbonate (56.73 g, 410.3 mmol) and the mixture was heated at 105° C. for 12 hours. The mixture was cooled to room temperature and the solid was filtered off The filtrate was evaporated till dryness. The crude product was purified by column chromatography (silica gel; DCM to DCM/EtOAc up to 20% as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate 3 (13.18 g, 46%).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationthe solid was filtered off The filtrate
  3. customwas evaporated till dryness
  4. customThe crude product was purified by column chromatography (silica gel; DCM to DCM/EtOAc up to 20% as eluent)
  5. customThe desired fractions were collected
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-19baa36cf228409a8f37bc71082ba742
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906939B2

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