Sodium Bicarbonate → HCID 22989223, compound

HRID 1067550Notes

Reaction equation

HRID 1067550 reaction equation
[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:25][C:26]1[CH:27]=[CH:28][C:29]2[N:30]([CH:32]=[C:33]([C:35]3([C:38]([O:40][CH:41]([CH3:43])[CH3:42])=[O:39])[CH2:37][CH2:36]3)[N:34]=2)[N:31]=1.C(=O)(O)[O-].[Na+]>>[ClH:25].[ClH:25].[C:19]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:26]3[CH:27]=[CH:28][C:29]4[N:30]([CH:32]=[C:33]([C:35]5([C:38]([O:40][CH:41]([CH3:43])[CH3:42])=[O:39])[CH2:37][CH2:36]5)[N:34]=4)[N:31]=3)[CH2:11][CH2:10]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamineHCID 22989336HCID 22989336, compound

Product 1

HCID 22989223HCID 22989223, compoundYield 49.1%

Procedure

2.72 g of 4-(diphenylmethoxy)-1-piperidinepropanamine and 1.27 g of isopropyl 1-(6-chloroimidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxylate were stirred at 165° C. for 4.5 hours. After cooling, aqueous sodium bicarbonate was added, followed by extraction with ethyl acetate; the extract was washed with saturated saline and dried with magnesium 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 (50:5:1). The desired fraction was collected, concentrated under reduced pressure and dissolved in 5 ml of ethyl acetate; 0.72 ml of a 4 N solution of hydrogen chloride in ethyl acetate was added, followed by concentration again. The residue was crystallized by the addition of ethyl acetate-acetone (2:1), collected by filtration, washed with ethyl acetate and dried to yield 714 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 with magnesium sulfate
  5. concentrationThe dry product was concentrated 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. addition0.72 ml of a 4 N solution of hydrogen chloride in ethyl acetate was added
  11. concentrationfollowed by concentration again
  12. customThe residue was crystallized by the addition of ethyl acetate-acetone (2:1)
  13. filtrationcollected by filtration
  14. washwashed with ethyl acetate
  15. customdried

Sources & evidence

ORD record
ord-4720aa14e0da401f96b314abfea422d0
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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