Ethyl Acetate → 3-[2-{2-(N-carboxymethyl-N-methylcarbamoyl)methyl-1-cyclohexenyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

HRID 965353Notes

Reaction equation

HRID 965353 reaction equation
C([O:3][C:4]([CH2:6][N:7]([CH3:39])[C:8]([CH2:10][C:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=1[N:17]1[C:22](=[O:23])[CH:21]=[CH:20][C:19]([C:24]2[C:25]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[N:26][N:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=23)=[N:18]1)=[O:9])=[O:5])C.[OH-].[Na+].C(OCC)(=O)C>O1CCOCC1.O>[C:4]([CH2:6][N:7]([CH3:39])[C:8]([CH2:10][C:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=1[N:17]1[C:22](=[O:23])[CH:21]=[CH:20][C:19]([C:24]2[C:25]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[N:26][N:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=23)=[N:18]1)=[O:9])([OH:5])=[O:3]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 226292113-[2-{2-(N-ethoxycarbonylmethyl-N-methylcarbamoyl)methyl-1-cyclohexenyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

Product 1

HCID 226291853-[2-{2-(N-carboxymethyl-N-methylcarbamoyl)methyl-1-cyclohexenyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridineYield 44.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-[2-{2-(N-ethoxycarbonylmethyl-N-methylcarbamoyl)methyl-1-cyclohexenyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (710 mg) in a mixture of dioxane (7 ml) and water (4 ml) was added 1N-aqueous sodium hydroxide solution (3.4 ml), which was stirred for two hours at room temperature. The reaction mixture was poured into ethyl acetate (100 ml) and aqueous layer was collected, which was adjusted to pH 1.5 with 6N-aqueous hydrochloric acid and extracted with ethyl acetate (100 ml×2). Organic layers were combined, washed in turn with water (50 ml×3) and brine (50 ml×2), and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (80 ml) eluting in turn with dichloromethane, 5%, 10%, 15% methanol in dichloromethane. Fractions containing desired product were collected. Evaporation of the solvent gave a residue, which was recrystallized from a mixture of dichloromethane and n-hexane to give 3-[2-{2-(N-carboxymethyl-N-methylcarbamoyl)methyl-1-cyclohexenyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (300 mg).

Workup

  1. customwas collected
  2. extractionextracted with ethyl acetate (100 ml×2)
  3. washwashed in turn with water (50 ml×3) and brine (50 ml×2)
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customgave a residue, which
  7. customwas chromatographed on silica gel (80 ml)
  8. washeluting in turn with dichloromethane, 5%, 10%, 15% methanol in dichloromethane
  9. additionFractions containing desired product
  10. customwere collected
  11. customEvaporation of the solvent
  12. customgave a residue, which
  13. customwas recrystallized from a mixture of dichloromethane and n-hexane

Sources & evidence

ORD record
ord-a0238eb8f5da42ba98a3f9e5462f2054
Source dataset
uspto-grants-1998_06
Patent number
US05773530

Reaction notes

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