Sodium Bicarbonate → HCID 22989244, compound

HRID 1067575Notes

Reaction equation

HRID 1067575 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 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: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. Ethylether was added to the residue; the powder was collected by filtration and dried to yield 216 mg of the title compound. amorphous

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe extract was washed with saturated saline
  4. dry with materialdried with magnesium sulfate
  5. concentrationThe solution was concentrated 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. additionEthylether was added to the residue
  13. filtrationthe powder was collected by filtration
  14. customdried

Sources & evidence

ORD record
ord-c1a879f232624b3f9239a405d884d554
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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