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

HRID 597858Notes

Reaction equation

HRID 597858 reaction equation
[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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-55f75c1b8e9e451794af892db489d4da
Source dataset
uspto-grants-2011_03
Patent number
US07897600B2

Reaction notes

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