Sodium Hydroxide → HCID 23000295, compound

HRID 397582Notes

Reaction equation

HRID 397582 reaction equation
[C:1]1([CH:7]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19]3[CH:20]=[CH:21][C:22]4[N:23]([C:25](=[O:36])[N:26]([C:28]([CH3:35])([CH3:34])[C:29]([O:31]CC)=[O:30])[N:27]=4)[N:24]=3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:37]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][NH:18][C:19]3[CH:20]=[CH:21][C:22]4[N:23]([C:25](=[O:36])[N:26]([C:28]([CH3:35])([CH3:34])[C:29]([OH:31])=[O:30])[N:27]=4)[N:24]=3)[CH2:13][CH2:14]2)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23000312HCID 23000312, compound

Product 1

HCID 23000295HCID 23000295, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.50 g of ethyl 2-[6-[3-[4-(diphenylmethoxy)piperidino]propylamino]-3-oxo[1,2,4]triazolo[4,3-b]pyridazin-2(3H)-yl]-2-methylpropionate was dissolved in 3 ml of ethanol; 2.2 ml of a 1 N aqueous solution of sodium hydroxide was added, followed by stirring at room temperature for 24 hours. After the ethanol was distilled off under reduced pressure, the residue was diluted with water and washed with ethyl acetate. To the water layer, 2.2 ml of 1 N hydrochloric acid was added; the mixture was saturated with sodium chloride and extracted with ethyl acetate-tetrahydrofuran (2:1); the extract was washed with saturated saline and dried over magnesium sulfate. After concentration under reduced pressure, the residue was powdered by the addition of ethyl acetate, collected by filtration, washed with ethyl acetate, and dried, to yield 0.203 g of the title compound.

Workup

  1. distillationAfter the ethanol was distilled off under reduced pressure
  2. additionthe residue was diluted with water
  3. washwashed with ethyl acetate
  4. additionTo the water layer, 2.2 ml of 1 N hydrochloric acid was added
  5. extractionextracted with ethyl acetate-tetrahydrofuran (2:1)
  6. washthe extract was washed with saturated saline
  7. dry with materialdried over magnesium sulfate
  8. concentrationAfter concentration under reduced pressure
  9. additionthe residue was powdered by the addition of ethyl acetate
  10. filtrationcollected by filtration
  11. washwashed with ethyl acetate
  12. customdried

Sources & evidence

ORD record
ord-d19a5bc7388f44cdb6b51ab334a88387
Source dataset
uspto-grants-2003_08
Patent number
US06610694B1

Reaction notes

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