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

HRID 876866

반응식

HRID 876866 반응식
[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

참가 물질

7

반응물 3

HCID 121282-Chloro-1,1-diethoxyethane2회HCID 569536546-Chloro-5-phenylpyridazin-3-amineHCID 768487136-Chloro-4-phenylpyridazin-3-amine

생성물 1

HCID 569536556-Chloro-7-phenyl-imidazo[1,2-b]pyridazine수율 30.1%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d6cdce00935d4a2394bb40f3010cff29
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987273B2

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