Reaktionsgleichung
[Cl:1]C(C=O)C(OCC)=O.BrC1C=C(Cl)N=NC=1N.Br[C:20]1[C:21]2[N:22]([C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][N:29]=2)[N:23]=[C:24]([Cl:26])[CH:25]=1>>[Cl:26][C:24]1[CH:25]=[C:20]([Cl:1])[C:21]2[N:22]([C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][N:29]=2)[N:23]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
To a 250 mL round-bottomed flask was added ethyl 2-chloro-3-oxopropanoate (4.33 g, 28.8 mmol) and 4-bromo-6-chloropyridazin-3-amine (5 g, 23.99 mmol). The solution was heated to 90° C. for 16 hours. The solution was quenched with ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The crude material was purified by ISCO (10% ethyl acetate/dichloromethane; 80 g column) to give a mixture of ethyl 8-bromo-6-chloroimidazo[1,2-b]pyridazine-3-carboxylate and ethyl 6,8-dichloroimidazo[1,2-b]pyridazine-3-carboxylate (2.1 g, 29% yield). LC/MS, m/z 256.96 (M+1). HPLC Rt, 2.54 min. LC/MS, m/z 303.92 (M+1). HPLC Rt, 2.63 min. Waters Sunfire C18 column (4.6×50 mm) 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B=0, final % B=100, gradient time 4 min, hold at 100% B 1 min, flow rate 4 mL/min.
Aufarbeitung
- customThe solution was quenched with ethyl acetate
- washwashed with water
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customThe crude material was purified by ISCO (10% ethyl acetate/dichloromethane; 80 g column)
- customto give
Quellen und Nachweise
- ORD-Eintrag
- ord-ee428c6a52754a0fb7cf030865aa817b
- Quelldatensatz
- uspto-grants-2013_03
- Patentnummer
- US08389527B2
Verknüpfte Notizen
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