Ethyl Acetate → 6-[4-[4-(Diphenylmethoxy)piperidino]butylamino][1,2,4]triazolo[4,3-b]pyridazine

HRID 397557

Reaction equation

HRID 397557 reaction equation
[C:1]1([CH:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:27]1[CH:28]=[CH:29][C:30]2[N:31]([CH:33]=[N:34][N:35]=2)[N:32]=1.C(N(C(C)C)C(C)C)C.C(OCC)(=O)C>C(O)CCC>[C:20]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][CH2:18][NH:19][C:27]3[CH:28]=[CH:29][C:30]4[N:31]([CH:33]=[N:34][N:35]=4)[N:32]=3)[CH2:11][CH2:10]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 3136246-Chloro-[1,2,4]triazolo[4,3-b]pyridazineHCID 117392591-Piperidinebutanamine, 4-(diphenylmethoxy)-

Product 1

HCID 155241516-[4-[4-(Diphenylmethoxy)piperidino]butylamino][1,2,4]triazolo[4,3-b]pyridazineYield 39.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

1.15 g of 4-(diphenylmethoxy)-1-piperidinebutanamine and 578 mg of 6-chloro[1,2,4]triazolo[4,3-b]pyridazine were dissolved in 20 ml of 1-butanol; 1.17 ml of N-ethyldiisopropylamine was added, followed by refluxing under heating for 14 hours. After cooling, ethyl acetate was added; the reaction mixture was washed with aqueous sodium bicarbonate and 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 (50:5:1). The desired fraction was collected and concentrated under reduced pressure; the residue was crystallized from ethyl acetate and dried to yield 611 mg of the title compound.

Workup

  1. temperatureby refluxing
  2. temperatureunder heating for 14 hours
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with aqueous sodium bicarbonate and saturated saline
  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. customthe residue was crystallized from ethyl acetate
  11. customdried

Sources & evidence

ORD record
ord-b5bf99c2ffe947f096ecd639dfe4e842
Source dataset
uspto-grants-2003_08
Patent number
US06610694B1

Linked notes

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