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

HRID 397556

Reaction equation

HRID 397556 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[N:9][N:10]=2)[N:7]=1.[C:11]1([CH:17]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][NH2:28])[CH2:21][CH2:20]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(C(C)C)C(C)C)C.C(=O)([O-])O.[Na+]>C(O)CCC>[C:29]1([CH:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][NH:28][C:2]3[CH:3]=[CH:4][C:5]4[N:6]([CH:8]=[N:9][N:10]=4)[N:7]=3)[CH2:21][CH2:20]2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 3136246-Chloro-[1,2,4]triazolo[4,3-b]pyridazineHCID 516892Sodium BicarbonateHCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamine

Product 1

HCID 155241506-[3-(4-(Diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[4,3-b]pyridazineYield 48.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

0.464 g of 6-chloro[1,2,4]triazolo[4,3-b]pyridazine and 1.26 g of 4-(diphenylmethoxy)-1-piperidinepropanamine were suspended in 20 ml of 1-butanol; 0.62 ml of N-ethyldiisopropylamine was added, followed by refluxing under heating for 12 hours. After ice water and 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 washed with ethyl acetate and dried to yield 0.648 g of the title compound.

Workup

  1. temperatureby refluxing
  2. temperatureunder heating for 12 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washthe extract was washed with saturated saline
  5. dry with materialdried over magnesium sulfate
  6. concentrationAfter concentration under reduced pressure
  7. washeluted with ethyl acetate-methanol-triethylamine (90:10:1)
  8. customThe desired fraction was collected
  9. concentrationconcentrated
  10. customthe crystal obtained
  11. washwas washed with ethyl acetate
  12. customdried

Sources & evidence

ORD record
ord-4d3147e3bb5844ada7c54f1b19c9dd47
Source dataset
uspto-grants-2003_08
Patent number
US06610694B1

Linked notes

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