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

HRID 876866

反応式

HRID 876866 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d6cdce00935d4a2394bb40f3010cff29
出典データセット
uspto-grants-2015_03
特許番号
US08987273B2

関連ノート

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