Reaktionsgleichung
C[N:2]([CH:4]=[C:5]1[C:10](=[O:11])[CH:9]=[C:8]([CH3:12])[O:7][C:6]1=[O:13])[CH3:3].Cl.[C:15]([C:17]1[CH:24]=[CH:23][C:20](CN)=[CH:19][CH:18]=1)#[N:16].CC(C)([O-])C.[Na+].Cl>C(O)C>[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH2:3][N:2]2[C:8]([CH3:12])=[CH:9][C:10](=[O:11])[C:5]([C:6]([OH:7])=[O:13])=[CH:4]2)=[CH:19][CH:18]=1)#[N:16]Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 3-dimethylaminomethylene-6-methyl-pyran-2,4-dione (preparation 1a, 2.00 g, 9.38 mmol based on 85% purity), 4-cyanobenzylamine hydrochloride (4.00 mL, 23.7 mmol) and sodium tert-butoxide (2.74 g, 28.5 mmol) in ethanol (11 mL) is heated for 48 h at 90° C. The reaction mixture is acidified with 4N aqueous HCl and extracted several times with dichloromethane. The combined organic layer is dried over Na2SO4, evaporated under reduced pressure and purified by preparative reversed-phase HPLC (Sunfire, gradient of methanol in water, 0.1% TFA, 60° C.). Yield: 0.94 g (37% of theory); ESI mass spectrum: [M+H]+=269; Retention time HPLC: 0.86 min (Z002—005).
Aufarbeitung
- extractionextracted several times with dichloromethane
- dry with materialThe combined organic layer is dried over Na2SO4
- customevaporated under reduced pressure
- custompurified by preparative reversed-phase HPLC (Sunfire, gradient of methanol in water, 0.1% TFA, 60° C.)
- custom0.86 min (Z002—005)
Quellen und Nachweise
- ORD-Eintrag
- ord-1b72d0823ea248539d5f0eea4d1780f9
- Quelldatensatz
- uspto-grants-2015_08
- Patentnummer
- US09102624B2
Verknüpfte Notizen
Wird geladen…