6-{1-[6-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-vinyl}-quinoline → HCID 44465539, compound

HRID 69200Notes

Reaction equation

HRID 69200 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([C:16]([C:18]4[CH:19]=[C:20]5[C:25](=[CH:26][CH:27]=4)[N:24]=[CH:23][CH:22]=[CH:21]5)=[CH2:17])=[CH:14][N:15]=3)[N:12]=2)[CH:4]=[N:3]1>C(O)C.[Pd]>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH:16]([C:18]4[CH:19]=[C:20]5[C:25](=[CH:26][CH:27]=4)[N:24]=[CH:23][CH:22]=[CH:21]5)[CH3:17])=[CH:14][N:15]=3)[N:12]=2)[CH:4]=[N:3]1

Participants

4

Reactant 1

HCID 579174486-{1-[6-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-vinyl}-quinoline

Product 1

HCID 44465539HCID 44465539, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-{1-[6-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-vinyl}-quinoline (Example 155, 2.2 g, 6.24 mmol) was dissolved in ethanol (300 mL) and hydrogenated under H2 atm. at rt in presence of Pd/5% C. After 10 h, the RM was filtered over Celite and the filtrate evaporated under vacuo. The residue was dried over night under vacuo and eluted on a silica gel column with EtOAc/MeOH=9:1 then 85:15 to afford, after evaporation of the solvent, the title compound as a yellow foam (tR 3.21 min (conditions 3), MH+=355).

Workup

  1. customat rt
  2. filtrationthe RM was filtered over Celite
  3. customthe filtrate evaporated under vacuo
  4. customThe residue was dried over night under vacuo
  5. washeluted on a silica gel column with EtOAc/MeOH=9:1
  6. custom85:15 to afford
  7. customafter evaporation of the solvent

Sources & evidence

ORD record
ord-8fc6a28ed3db4422b01baa3a6d0b6a2f
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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