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Sodium Bicarbonate → HCID 22989407, compound

HRID 1067528
Notes
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Reaction equation

HRID 1067528 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]([CH3:40])([CH3:39])[C:36]([NH2:38])=[O:37])[N:34]=2)[N:31]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[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]([CH3:40])([CH3:39])[C:36]([NH2:38])=[O:37])[N:34]=4)[N:31]=3)[CH2:11][CH2:10]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamineHCID 11831504HCID 11831504, compound

Product 1

HCID 22989407HCID 22989407, compoundYield 137.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.29 g of 4-(diphenylmethoxy)-1-piperidinepropanamine and 0.478 g of 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl]-2-methylpropionamide were stirred at 190-200° C. for 70 minutes. After cooling, aqueous sodium bicarbonate was added, followed by.,extraction with ethyl acetate. The extract was washed with 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 (90:10:1). The desired fraction was collected; the residue was dissolved in 10 ml of ethyl acetate; 1.5 ml of a 4 N hydrogen chloride solution in ethyl acetate was added, followed by concentration under reduced pressure. Ethyl acetate was added to the residue; the resulting powder was collected by filtration, washed with ethyl acetate and dried to yield 0.823 g of the title compound.

Workup

  1. temperatureAfter cooling
  2. washThe extract was washed with saline
  3. dry with materialdried with magnesium sulfate
  4. concentrationThe dry product was concentrated under reduced pressure
  5. washeluted with ethyl acetate:methanol:triethylamine (90:10:1)
  6. customThe desired fraction was collected
  7. dissolutionthe residue was dissolved in 10 ml of ethyl acetate
  8. addition1.5 ml of a 4 N hydrogen chloride solution in ethyl acetate was added
  9. concentrationfollowed by concentration under reduced pressure
  10. additionEthyl acetate was added to the residue
  11. filtrationthe resulting powder was collected by filtration
  12. washwashed with ethyl acetate
  13. customdried

Sources & evidence

ORD record
ord-0351af6ecdb143fead9bc7d42112d710
Source dataset
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06248740B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes