Sodium Hydroxide → HCID 15158132, compound

HRID 466022Notes

Reaction equation

HRID 466022 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][N:7]1[C:12](=[O:13])[CH2:11][CH2:10][C:9]([C:14]2[C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:16][N:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=23)=[N:8]1)=[O:4].[OH-].[Na+]>CO>[C:3]([CH2:5][CH2:6][N:7]1[C:12](=[O:13])[CH2:11][CH2:10][C:9]([C:14]2[C:15]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[N:16][N:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=23)=[N:8]1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15158126HCID 15158126, compound

Product 1

HCID 15158132HCID 15158132, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-[2-(2-methoxycarbonylethyl)-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (484 mg), 1N sodium hydroxide aqueous solution (2.1 ml) and methanol (5 ml) was stirred at room temperature for 1 hour. Methanol was evaporated in vacuo. To the residue, water (10 ml) was added and the solution was acidified with 5% hydrochloric acid and extracted with chloroform (20 ml×2). The combined extracts was washed with a saturated aqueous solution of sodium chloride (20 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel using a mixture of chloroform and methanol (30:1) as an eluent to give 3-[2-(2-carboxyethyl)-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (198 mg) as an oil. This free acid was dissolved in a mixture of 1N sodium hydroxide aqueous solution (0.547 mg) and ethanol (3 ml), and the solvent was evaporated in vacuo. The residue was triturated with 95% ethanol, collected by filtration, washed with acetone and dried to give powder of sodium salt of 3-[2-(2-carboxyethyl)-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (129 mg).

Workup

  1. customMethanol was evaporated in vacuo
  2. additionTo the residue, water (10 ml) was added
  3. extractionextracted with chloroform (20 ml×2)
  4. washThe combined extracts was washed with a saturated aqueous solution of sodium chloride (20 ml)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel using
  8. additiona mixture of chloroform and methanol (30:1) as an eluent

Sources & evidence

ORD record
ord-f52b31bbf2024641b070b852139aa1fc
Source dataset
uspto-grants-1992_10
Patent number
US05155114

Reaction notes

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