Diisopropylethylamine → 6-[3-[4-(Diphenylmethoxy)piperidino]propylamino]-2-phenyl[1,2,4]triazolo[1,5-b]pyridazine

HRID 1169037Notes

Reaction equation

HRID 1169037 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[N:7]=1.[C:17]1([CH:23]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:24][CH:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][NH2:34])[CH2:27][CH2:26]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)C(C)C)C.C(=O)([O-])O.[Na+]>C(O)CCC>[C:35]1([CH:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:24][CH:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][NH:34][C:2]3[CH:3]=[CH:4][C:5]4[N:6]([N:8]=[C:9]([C:11]5[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=5)[N:10]=4)[N:7]=3)[CH2:27][CH2:26]2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 14591196-Chloro-2-phenyl-[1,2,4]triazolo[1,5-b]pyridazineHCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamine

Product 1

HCID 229893166-[3-[4-(Diphenylmethoxy)piperidino]propylamino]-2-phenyl[1,2,4]triazolo[1,5-b]pyridazineYield 37.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

365 mg of 6-chloro-2-phenyl[1,2,4]triazolo[1,5-b]pyridazine and 0.513 g of 4-(diphenylmethoxy)-1-piperidinepropanamine were suspended in 8 ml of 1-butanol; 0.54 ml of N-ethyldiisopropylamine was added, followed by heating and refluxing for 19 hours. Ice water and sodium hydrogen carbonate were added, followed by extraction with ethyl acetate; the extract was washed with saturated saline, dried over magnesium sulfate and 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 and concentrated; the resulting crystal was recrystallized from ethyl acetate to yield 308 mg of the title compound.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 19 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washthe extract was washed with saturated saline
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluted with ethyl acetate:methanol:triethylamine (50:5:1)
  8. customThe desired fraction was collected
  9. concentrationconcentrated
  10. customthe resulting crystal was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fcdd091e088a4c8c962258da02ec77d4
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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