Sodium Bicarbonate → HCID 22989244, compound

HRID 1169109Notes

Reaction equation

HRID 1169109 reaction equation
[OH:1][C:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11][NH2:12])[CH2:5][CH2:4]1.[Cl:25][C:26]1[CH:27]=[CH:28][C:29]2[N:30]([CH:32]=[C:33]([C:35]([CH3:42])([CH3:41])[C:36]([O:38][CH2:39][CH3:40])=[O:37])[N:34]=2)[N:31]=1.C(=O)(O)[O-].[Na+]>C(O)C>[ClH:25].[ClH:25].[OH:1][C:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH:3]1[CH2:4][CH2:5][N:6]([CH2:9][CH2:10][CH2:11][NH:12][C:26]2[CH:27]=[CH:28][C:29]3[N:30]([CH:32]=[C:33]([C:35]([CH3:41])([CH3:42])[C:36]([O:38][CH2:39][CH3:40])=[O:37])[N:34]=3)[N:31]=2)[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11034698HCID 11034698, compoundHCID 11043751Ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropanoate

Product 1

HCID 22989244HCID 22989244, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

427 mg of 4-(hydroxydiphenylmethyl)-1-piperidinepropanamine and 235 mg of ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropionate were stirred at 160° C. for 3.5 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 and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate:methnol:triethylamine (50:5:1). The desired fraction was collected, concentrated, dissolved in 5 ml of ethyl acetate; 0.23 ml of 4N-hydrogenchloride in ethyl acetate was added, followed by concentration. Ethyl ether was added to the residue; the powder was collected by filtration and dried to yield 216 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
  7. customThe desired fraction was collected
  8. concentrationconcentrated
  9. dissolutiondissolved in 5 ml of ethyl acetate
  10. addition0.23 ml of 4N-hydrogenchloride in ethyl acetate was added
  11. concentrationfollowed by concentration
  12. additionEthyl ether was added to the residue
  13. filtrationthe powder was collected by filtration
  14. customdried

Sources & evidence

ORD record
ord-0eedd170ef76464482089548f1c7402c
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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