Ethanol → (8-(Aminomethyl)-6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)(4-chloro-2-fluorophenyl)methanone

HRID 597858ノート

反応式

HRID 597858 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:22][N:23]2C(=O)C3C(=CC=CC=3)C2=O)[C:5]2[N:6]([C:8]([C:12](=[O:21])[C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[F:20])=[C:9]([CH3:11])[N:10]=2)[N:7]=1.C(O)C.NN>CC(=O)OCC>[NH2:23][CH2:22][C:4]1[C:5]2[N:6]([C:8]([C:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[F:20])=[O:21])=[C:9]([CH3:11])[N:10]=2)[N:7]=[C:2]([Cl:1])[CH:3]=1

参加物

5

反応物 3

HCID 702EthanolHCID 9321HydrazineHCID 866424872-((6-Chloro-3-(4-chloro-2-fluorobenzoyl)-2-methylimidazo[1,2-b]pyridazin-8-yl)methyl)isoindoline-1,3-dione

生成物 1

HCID 86642486(8-(Aminomethyl)-6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)(4-chloro-2-fluorophenyl)methanone

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Combine 2-((6-chloro-3-(4-chloro-2-fluorobenzoyl)-2-methylimidazo[1,2-b]pyridazin-8-yl)methyl)isoindoline-1,3-dione (7.30 g, 15.1 mmol), ethanol (200 mL), and hydrazine (1.45 mL, 3 equiv.) in a round bottom flask and place under nitrogen. Stir for 2 days at RT. Heat for 2 h at 50° C. then concentrate the reaction in vacuo. Dilute with EA. Wash the organics with 1 N HCl (aq) to pull product into the aqueous layer. Make the aqueous layer basic with 1 N NaOH (aq) and extract with EA. Wash the EA layer with aqueous saturated sodium chloride, and dry over anhydrous magnesium sulfate. Filter and concentrate in vacuo to give the title compound crude (1.2 g, 23%) as a light green solid. MS=355.0, 353.0 (M+1).

後処理

  1. temperatureHeat for 2 h at 50° C.
  2. concentrationthen concentrate
  3. customthe reaction in vacuo
  4. washWash the organics with 1 N HCl (aq)
  5. extractionextract with EA
  6. washWash the EA layer with aqueous saturated sodium chloride
  7. dry with materialdry over anhydrous magnesium sulfate
  8. filtrationFilter
  9. concentrationconcentrate in vacuo

出典と根拠

ORDレコード
ord-55f75c1b8e9e451794af892db489d4da
出典データセット
uspto-grants-2011_03
特許番号
US07897600B2

反応ノート

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