4-(Diphenylmethoxy)-1-piperidinepropaneamine → Ethyl 6-[3-[4-(diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[4,3-b]pyridazine-3-carboxylate

HRID 397563Notes

Reaction equation

HRID 397563 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[C:26]1[CH:27]=[CH:28][C:29]2[N:30]([C:32]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[N:33][N:34]=2)[N:31]=1>CN(C)C=O>[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]([C:32]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[N:33][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 2

HCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamineHCID 11287584Ethyl 6-chloro-(1,2,4)triazolo(4,3-b)pyridazine-3-carboxylate

Product 1

HCID 23000327Ethyl 6-[3-[4-(diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[4,3-b]pyridazine-3-carboxylateYield 26.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

5.15 g of 4-(diphenylmethoxy)-1-piperidinepropanamine and 3.6 g of ethyl 6-chloro[1,2,4]triazolo[4,3-b]pyridazine-3-carboxylate were dissolved in 70 ml of N,N-dimethylformamide; 5.48 ml of N-ethyldiisdpropylamine was added, followed by stirring under heating at an external temperature of 70° C. for 4 hours. After cooling, cold saline was added; the reaction mixture was extracted with tetrahydrofuran and dried over magnesium sulfate. After concentration 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 and concentrated under reduced pressure; half of the precipitated crystal was recrystallized from ethanol-ethyl acetate (1:1), collected by filtration, and dried, to yield 2.13 g of the title compound.

Workup

  1. addition5.48 ml of N-ethyldiisdpropylamine was added
  2. temperatureAfter cooling
  3. additioncold saline was added
  4. extractionthe reaction mixture was extracted with tetrahydrofuran
  5. dry with materialdried over magnesium sulfate
  6. concentrationAfter concentration under reduced pressure
  7. washeluted with ethyl acetate-methanol-triethylamine (50:5:1)
  8. customThe desired fraction was collected
  9. concentrationconcentrated under reduced pressure
  10. customhalf of the precipitated crystal was recrystallized from ethanol-ethyl acetate (1:1)
  11. filtrationcollected by filtration
  12. customdried

Sources & evidence

ORD record
ord-73b276458b924d729d472013eec73ed5
Source dataset
uspto-grants-2003_08
Patent number
US06610694B1

Reaction notes

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