Ethanol → HCID 22989425, compound

HRID 1169108Notes

Reaction equation

HRID 1169108 reaction equation
[C:1]1([N:7]([CH2:18][C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH2:17])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:24][C:25]1[CH:26]=[CH:27][C:28]2[N:29]([CH:31]=[C:32]([C:34]([CH3:41])([CH3:40])[C:35]([O:37][CH2:38][CH3:39])=[O:36])[N:33]=2)[N:30]=1.C(O)C.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[ClH:24].[ClH:24].[ClH:24].[C:1]1([N:7]([CH2:18][C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:25]3[CH:26]=[CH:27][C:28]4[N:29]([CH:31]=[C:32]([C:34]([CH3:40])([CH3:41])[C:35]([O:37][CH2:38][CH3:39])=[O:36])[N:33]=4)[N:30]=3)[CH2:10][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 11043751Ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropanoateHCID 22989335HCID 22989335, compound

Product 1

HCID 22989425HCID 22989425, compoundYield 124.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
170 °C

Procedure

1.44 g of 4-[phenyl(2-thienyl)methylamino]-1-piperidinepropanamine and 585 mg of ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropionate were dissolved in 3 ml of 1-methyl-2-pyrrolidone, followed by stirring in an oil bath (170° C.) for 4 hours. After cooling, ethanol and saturated aqueous sodium bicarbonate were added, followed by extraction with ethyl acetate; the extract was washed with saturated saline, dried over magnesium sulfate. The solution was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate:methanol:triethylamine (50:5:1). The desired fraction was collected, concentrated, dissolved in 5 ml of ethyl acetate; 0.86 ml of 4N-hydrogenchloride in ethyl acetate was added, followed by concentration. Ethanol-ethyl acetate (1:4) was added to the residue; the crystal precipitated was collected by filtration and dried to yield 609 mg of the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe extract was washed with saturated saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solution was concentrated under reduced pressure
  6. washeluted with ethyl acetate:methanol:triethylamine (50:5:1)
  7. customThe desired fraction was collected
  8. concentrationconcentrated
  9. dissolutiondissolved in 5 ml of ethyl acetate
  10. addition0.86 ml of 4N-hydrogenchloride in ethyl acetate was added
  11. concentrationfollowed by concentration
  12. additionEthanol-ethyl acetate (1:4) was added to the residue
  13. customthe crystal precipitated
  14. filtrationwas collected by filtration
  15. customdried

Sources & evidence

ORD record
ord-d839c56fdfe84a58b4dfdb68feb69aae
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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