2-Chloro-1,1-diethoxyethane → 6-Chloro-7-phenyl-imidazo[1,2-b]pyridazine

HRID 876866

Reaktionsgleichung

Reaktionsgleichung von HRID 876866
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl[C:16]1N=NC(N)=C(C2C=CC=CC=2)[CH:17]=1.C(OC(OCC)CCl)C>O.C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:5]2[N:6]([CH:16]=[CH:17][N:8]=2)[N:7]=1

Komponenten

7

Edukt 3

HCID 121282-Chloro-1,1-diethoxyethane2×HCID 569536546-Chloro-5-phenylpyridazin-3-amineHCID 768487136-Chloro-4-phenylpyridazin-3-amine

Produkt 1

HCID 569536556-Chloro-7-phenyl-imidazo[1,2-b]pyridazineAusbeute 30,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The mixture of 6-chloro-5-phenyl-pyridazin-3-yl-amine and 6-chloro-4-phenyl-pyridazin-3-yl-amine (20.2 g=0.1 mol) was suspended in 300 mL water and 30 mL THF. After addition of 32 mL (0.51 mol) chloracetaldehyde diethylacetal the reaction mixture was heated for five hours at reflux. Additional 32 mL (0.51 mol) chloracetaldehyde diethylacetal were added and heating was continued for another six hours. The reaction mixture was diluted with ethyl acetate and extracted three times. The organic phase was dried (sodium sulfate), filtrated and the solvent was removed. The residue was purified by chromatography (Biotage, eluents: ethyl acetate/hexane). 6.8 g (30.1%) of the title compound, 6-chloro-7-phenyl-imidazo[1,2-b]pyridazine, and 6.4 g (28.4%) of the regioisomer, 6-chloro-8-phenyl-imidazo[1,2-b]pyridazine, were obtained.

Aufarbeitung

  1. temperaturewas heated for five hours
  2. temperatureat reflux
  3. temperatureheating
  4. extractionextracted three times
  5. dry with materialThe organic phase was dried (sodium sulfate)
  6. filtrationfiltrated
  7. customthe solvent was removed
  8. customThe residue was purified by chromatography (Biotage, eluents: ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d6cdce00935d4a2394bb40f3010cff29
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987273B2

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