Sodium Hydroxide → 2-[6-[3-[4-(Diphenylmethoxy)piperidino]propoxy][1,2,4]triazolo[4,3-b]pyridazin-3-yl]-2-methylpropionamide

HRID 397565Notes

Reaction equation

HRID 397565 reaction equation
[C:1]1([CH:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:20]=[CH:21][C:22]4[N:23]([C:25]([C:28]([CH3:32])([CH3:31])[C:29]#[N:30])=[N:26][N:27]=4)[N:24]=3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:39].[Na+]>CC(O)C>[C:33]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O:8][CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:20]=[CH:21][C:22]4[N:23]([C:25]([C:28]([CH3:32])([CH3:31])[C:29]([NH2:30])=[O:39])=[N:26][N:27]=4)[N:24]=3)[CH2:13][CH2:14]2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 230002962-[6-[3-[4-(Diphenylmethoxy)piperidino]propoxy][1,2,4]triazolo[4,3-b]pyridazin-3-yl]-2-methylpropionitrile

Product 1

HCID 230003102-[6-[3-[4-(Diphenylmethoxy)piperidino]propoxy][1,2,4]triazolo[4,3-b]pyridazin-3-yl]-2-methylpropionamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

409 mg of 2-[6-[3-[4-(diphenylmethoxy)piperidino]propoxy][1,2,4]triazolo[4,3-b]pyridazin-3-yl]-2-methylpropionitrile was dissolved in 6 ml of 2-propanol; 3.5 ml of a 1 N aqueous solution of sodium hydroxide was added, followed by stirring under heating at an external temperature of 40° C. for 12 hours. After cooling, the 2-propanol was distilled off; the residue was extracted with ethyl acetate-tetrahydrofuran (1:1), 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; the residue was crystallized from ethyl acetate-diethyl ether (1:1), washed with diethyl ether, and dried, to yield 293 mg of the title compound.

Workup

  1. temperatureAfter cooling
  2. distillationthe 2-propanol was distilled off
  3. extractionthe residue was extracted with ethyl acetate-tetrahydrofuran (1:1)
  4. washwashed with 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-diethyl ether (1:1)
  11. washwashed with diethyl ether
  12. customdried

Sources & evidence

ORD record
ord-02abcce3c41b410f8c12d81def453619
Source dataset
uspto-grants-2003_08
Patent number
US06610694B1

Reaction notes

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