Hydrochloric Acid → 6-(1-Isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-methoxy-5-phenyl-2-pyrazinecarbonitrile
Reaktionsgleichung
[CH3:1][O-:2].[Na+].[CH:4]([N:7]1[C:12](=[O:13])[CH:11]=[CH:10][C:9]([C:14]2[N:15]=[C:16]([C:28]#[N:29])[C:17](C#N)=[N:18][C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:8]1)([CH3:6])[CH3:5].Cl.O>CO.C(Cl)(Cl)Cl>[CH:4]([N:7]1[C:12](=[O:13])[CH:11]=[CH:10][C:9]([C:14]2[N:15]=[C:16]([C:28]#[N:29])[C:17]([O:2][CH3:1])=[N:18][C:19]=2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:8]1)([CH3:5])[CH3:6]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 27.5 °C
Versuchsvorschrift
To a solution of sodium methoxide (81.5 mg) in MeOH (3 ml), 5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-6-phenyl-2,3-pyrazinedicarbonitrile (172 mg) was added and the mixture was stirred at 25-30° C. for 10 hours. After addition of conc. HCl (1.5 ml), the reaction mixture was stirred at 25-30° C. for 20 hours. Water and CHCl3 were added to the mixture. An organic layer was collected, dried over MgSO4, concentrated under reduced pressure and subjected to column chromatography on silica gel. With elution of a mixture of n-hexane and EtOAc (70:30 v/v) was obtained 6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-methoxy-5-phenyl-2-pyrazinecarbonitrile as a solid (43 mg) and with elution of a mixture of n-hexane and EtOAc (50:50 v/v) was obtained methyl 6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-methoxy-5-phenyl-2-pyrazinecarboxylate as a solid (67 mg).
Aufarbeitung
- stirringthe reaction mixture was stirred at 25-30° C. for 20 hours
- customAn organic layer was collected
- dry with materialdried over MgSO4
- concentrationconcentrated under reduced pressure
- washWith elution of a mixture of n-hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-9a52cf92d51f4cf7902519adb3ab37e8
- Quelldatensatz
- uspto-grants-2007_09
- Patentnummer
- US07265120B2
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