Sodium Bicarbonate → HCID 22989277, compound

HRID 1067576Notes

Reaction equation

HRID 1067576 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:8][CH:9]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH2:17])[CH2:10]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)(O)[O-].[Na+]>CN1CCCC1=O>[ClH:24].[ClH:24].[C:18]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:9]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]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11043751Ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropanoateHCID 22989409HCID 22989409, compound

Product 1

HCID 22989277HCID 22989277, compoundYield 115.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
170 °C

Procedure

1.53 g of 3-(diphenylmethoxy)-1-pyrrolidinepropanamine and 660 mg of ehtyl 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 8 hours. After cooling, saturated aqueous sodium bicarbonate was added, followed by extraction with ethyl acetate; the extract was washed with water and saturated saline and dried with 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; 0.81 ml of 4N-hydrogenchloride in ethyl acetate was added, followed by concentration. Ethylether was added to the residue; the powder was collected by filtration and dried to yield 877 mg of the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe extract was washed with water and saturated saline
  4. dry with materialdried with 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. addition0.81 ml of 4N-hydrogenchloride in ethyl acetate was added
  11. concentrationfollowed by concentration
  12. additionEthylether was added to the residue
  13. filtrationthe powder was collected by filtration
  14. customdried

Sources & evidence

ORD record
ord-504e81196dc745eeb667c2326b8dd926
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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