Sodium Hydroxide → HCID 22629171, compound

HRID 276944Notes

Reaction equation

HRID 276944 reaction equation
C([O:8][C:9]([CH2:11][CH2:12][C:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=1[N:19]1[C:24](=[O:25])[CH:23]=[CH:22][C:21]([C:26]2[C:27]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[N:28][N:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=23)=[N:20]1)=[O:10])C1C=CC=CC=1.[OH-].[Na+]>O1CCCC1>[C:9]([CH2:11][CH2:12][C:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=1[N:19]1[C:24](=[O:25])[CH:23]=[CH:22][C:21]([C:26]2[C:27]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[N:28][N:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=23)=[N:20]1)([OH:10])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22629153HCID 22629153, compound

Product 1

HCID 22629171HCID 22629171, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-[2-{2-(2-benzyloxycarbonylethyl)-1-cyclohexenyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (74 mg) and 1N-sodium hydroxide (0.28 ml) in tetrahydrofuran (4 ml) was refluxed with stirring for 5 hours. The mixture was evaporated under reduced pressure. The residue was dissolved in water. The aqueous layer was washed with ethyl acetate, acidified with 1N-hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from ethanol-water to give 3-[2-{2-(2-carboxyethyl)-1-cyclohexenyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]-pyridine (54 mg).

Workup

  1. temperaturewas refluxed
  2. customThe mixture was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. washThe aqueous layer was washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-0ff63b1ae83c49f9ab6a9c0c9491ebe9
Source dataset
uspto-grants-2002_03
Patent number
US06355640B1

Reaction notes

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