6-{1-[6-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-vinyl}-quinoline → (Rac)-6-{1-[6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-ethyl}-1,2,3,4-tetrahydroquinoline

HRID 69199Notes

Reaction equation

HRID 69199 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)[NH:24][CH2:23][CH2:22][CH2:21]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 57917341(Rac)-6-{1-[6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-ethyl}-1,2,3,4-tetrahydroquinoline

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 15% 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, crystals of the title compound (tR 3.24 min (conditions 3), MH+=359).

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, crystals of the title compound (tR 3.24 min (conditions 3), MH+=359)

Sources & evidence

ORD record
ord-fdab832caa344e7c82907d8666a7d833
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

Loading…