Sodium Bicarbonate → HCID 69843561, compound

HRID 1067525Notes

Reaction equation

HRID 1067525 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[O:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][NH2:19])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.Cl[C:28]1[CH:29]=[CH:30][C:31]2[N:32]([CH:34]=[C:35]([C:37]([CH3:44])([CH3:43])[C:38]([O:40][CH2:41][CH3:42])=[O:39])[N:36]=2)[N:33]=1.[C:45](=[O:48])([OH:47])[O-].[Na+]>>[C:38]([OH:40])(=[O:39])/[CH:37]=[CH:35]/[C:45]([OH:47])=[O:48].[C:38]([OH:40])(=[O:39])/[CH:37]=[CH:35]/[C:45]([OH:47])=[O:48].[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[O:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][NH:19][C:28]3[CH:29]=[CH:30][C:31]4[N:32]([CH:34]=[C:35]([C:37]([CH3:43])([CH3:44])[C:38]([O:40][CH2:41][CH3:42])=[O:39])[N:36]=4)[N:33]=3)[CH2:12][CH2:11]2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 11043751Ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropanoateHCID 22989300HCID 22989300, compound

Product 1

HCID 69843561HCID 69843561, compound

Procedure

2.11 g of 4-[bis(4-methylphenyl)methoxy]-1-piperidinepropanamine and 0.803 g of ethyl 2-[6-chloroimidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate were stirred at 190-200° C. for 3 hours. After cooling, aqueous sodium bicarbonate was added, followed by extraction with ethyl acetate; the extract was washed with saturated saline and dried with sodium sulfate. The dry product was concentrated under reduced pressure; the residue was subjected to silica gel column chromatography and eluted with ethyl acetate:methanol:triethylamine (95:5:1). The desired fraction was collected, dissolved in 20 ml of ethyl acetate; a solution of 358 mg of fumaric acid in 20 ml of methanol was added, followed by concentration. Acetone was added to the residue; the crystal precipitated was collected by filtration, washed with acetone and dried to yield 0.901 g 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 with sodium sulfate
  5. concentrationThe dry product was concentrated under reduced pressure
  6. washeluted with ethyl acetate:methanol:triethylamine (95:5:1)
  7. customThe desired fraction was collected
  8. dissolutiondissolved in 20 ml of ethyl acetate
  9. additiona solution of 358 mg of fumaric acid in 20 ml of methanol was added
  10. concentrationfollowed by concentration
  11. additionAcetone was added to the residue
  12. customthe crystal precipitated
  13. filtrationwas collected by filtration
  14. washwashed with acetone
  15. customdried

Sources & evidence

ORD record
ord-1faa1f229fa34e73b0d050c6d241e939
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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