1-Butanol → 2-[6-[3-[4-(Diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[4,3-b]pyridazin-3-yl]-2-methylpropionitrile fumarate

HRID 397562Notes

Reaction equation

HRID 397562 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]([CH3:39])([CH3:38])[C:36]#[N:37])=[N:33][N:34]=2)[N:31]=1.C(N(C(C)C)C(C)C)C.[C:49]([O:52]CC)(=[O:51])[CH3:50].C([OH:59])CCC>>[C:7]([OH:59])(=[O:8])/[CH:19]=[CH:50]/[C:49]([OH:52])=[O:51].[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]([CH3:39])([CH3:38])[C:36]#[N:37])=[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

6

Reactant 5

HCID 2631-ButanolHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamineHCID 230002902-[6-Chloro[1,2,4]triazolo[4,3-b]pyridazin-3-yl)-2-methylpropionitrile

Product 1

HCID 230003412-[6-[3-[4-(Diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[4,3-b]pyridazin-3-yl]-2-methylpropionitrile fumarate

Procedure

5.57 g of 4-(diphenylmethoxy)-1-piperidinepropanamine and 3.62 g of 2-[6-chloro[1,2,4]triazolo[4,3-b]pyridazin-3-yl]-2-methylpropionitrile were dissolved in 60 ml of 1-butanol; 5.65 ml of N-ethyldiisopropylamine was added, followed by refluxing under heating for 3.5 hours. After cooling, ethyl acetate was added; the reaction mixture was washed with saturated aqueous sodium bicarbonate, 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 (50:5:1). The desired fraction was collected and concentrated under reduced pressure; 7.18 g of the residue was dissolved in ethanol; a solution of 1.59 g of fumaric acid in ethanol was added, followed by concentration under reduced pressure. The residue was powdered from diethyl ether and dried to yield 7.71 g of the title compound.

Workup

  1. temperatureby refluxing
  2. temperatureunder heating for 3.5 hours
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with saturated aqueous sodium bicarbonate
  5. washwashed with saturated saline
  6. dry with materialdried over magnesium sulfate
  7. concentrationAfter concentration under reduced pressure
  8. washeluted with ethyl acetate-methanol-triethylamine (50:5:1)
  9. customThe desired fraction was collected
  10. concentrationconcentrated under reduced pressure
  11. dissolution7.18 g of the residue was dissolved in ethanol
  12. additiona solution of 1.59 g of fumaric acid in ethanol was added
  13. concentrationfollowed by concentration under reduced pressure
  14. customdried

Sources & evidence

ORD record
ord-3dc5a6d1ddad40b3a05fa3c5a3be5276
Source dataset
uspto-grants-2003_08
Patent number
US06610694B1

Reaction notes

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