Sodium Bicarbonate → 6-[3-[4-(Diphenylmethoxy)piperidino]propylamino]-2-methyl[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

HRID 397574Notes

Reaction equation

HRID 397574 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8](=[O:12])[N:9]([CH3:11])[N:10]=2)[N:7]=1.[C:13]1([CH:19]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:20][CH:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][CH2:29][NH2:30])[CH2:23][CH2:22]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[C:31]1([CH:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:20][CH:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][CH2:29][NH:30][C:2]3[CH:3]=[CH:4][C:5]4[N:6]([C:8](=[O:12])[N:9]([CH3:11])[N:10]=4)[N:7]=3)[CH2:23][CH2:22]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamineHCID 230003286-chloro-2-methyl[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

Product 1

HCID 230003136-[3-[4-(Diphenylmethoxy)piperidino]propylamino]-2-methyl[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-oneYield 26.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
145 °C

Procedure

0.277 g of 6-chloro-2-methyl[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one was dissolved in 2 ml of N,N-dimethylformamide; 0.487 g of 4-(diphenylmethoxy)-1-piperidinepropanamine was added, followed by stirring in an oil bath (bath temperature 140-150° C.) for 1 hour. After cooling, ice water and an aqueous solution of sodium hydrogen carbonate were added; the reaction mixture was extracted with ethyl acetate; the extract was washed with saturated saline 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 (90:10:1). The desired fraction was collected and concentrated; the crystal obtained was filtered, washed with diethyl ether, and dried, to yield 0.19 g of the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washthe extract was washed with saturated saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationAfter concentration under reduced pressure
  6. washeluted with ethyl acetate-methanol-triethylamine (90:10:1)
  7. customThe desired fraction was collected
  8. concentrationconcentrated
  9. customthe crystal obtained
  10. filtrationwas filtered
  11. washwashed with diethyl ether
  12. customdried

Sources & evidence

ORD record
ord-606ce496be4749108b054af12afeffaa
Source dataset
uspto-grants-2003_08
Patent number
US06610694B1

Reaction notes

Loading…