Sodium Bicarbonate → HCID 22989344, compound

HRID 1169069Notes

Reaction equation

HRID 1169069 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N: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)(O)[O-].[Na+]>>[ClH:24].[ClH:24].[ClH:24].[C:18]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:9][CH2:10][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)[CH2:12][CH2:13]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 11043751Ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropanoateHCID 137677783-(4-Benzhydryl-1-piperazinyl)-1-propanamine

Product 1

HCID 22989344HCID 22989344, compoundYield 109.4%

Procedure

1.31 g of 4-(diphenylmethyl)-1-piperazinepropanamine and 567 mg of ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate were stirred at 185° C. for 3 hours. After cooling, aqueous sodium bicarbonate was added, followed by extraction with ethyl acetate; the extract was washed with saturated saline, dried over magnesium sulfate and 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 under reduced pressure and dissolved in 5 ml of ethyl acetate; 0.80 ml of a 4 N hydrogen chloride solution in ethyl acetate was added, followed by concentration again. Ethanol was added to the residue; the crystal precipitated was collected by filtration, washed with ethanol-ethyl acetate (1:3) and dried to yield 502 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. concentrationconcentrated under reduced pressure
  6. washeluted with ethyl acetate:methanol:triethylamine (50:5:1)
  7. customThe desired fraction was collected
  8. concentrationconcentrated under reduced pressure
  9. dissolutiondissolved in 5 ml of ethyl acetate
  10. addition0.80 ml of a 4 N hydrogen chloride solution in ethyl acetate was added
  11. concentrationfollowed by concentration again
  12. additionEthanol was added to the residue
  13. customthe crystal precipitated
  14. filtrationwas collected by filtration
  15. washwashed with ethanol-ethyl acetate (1:3)
  16. customdried

Sources & evidence

ORD record
ord-a2c3137d1833449f9318c49b757bfebb
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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