Sodium Hydroxide → HCID 54040846, compound

HRID 1742286Notes

Reaction equation

HRID 1742286 reaction equation
C([O:3][C:4]([CH2:6][NH:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[CH:14]=[CH:13][C:12]([C:17]2[C:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:19][N:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=23)=[N:11]1)=[O:5])C.[OH-].[Na+]>C(O)C.O>[C:4]([CH2:6][NH:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[CH:14]=[CH:13][C:12]([C:17]2[C:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:19][N:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=23)=[N:11]1)([OH:5])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54051188HCID 54051188, compound

Product 1

HCID 54040846HCID 54040846, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-[2-{2-(ethoxycarbonylmethylamino)ethyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.80 g) in ethanol (8 ml) was added a solution of sodium hydroxide (0.15 g) in water (4 ml) and the mixture was stirred for 0.5 hour at room temperature. The reaction mixture was concentrated and the residue was partitioned between water and ethyl acetate. The aqueous layer was separated, neutralized with 1N hydrochloric acid to give the precipitate, which was collected and purified by recrystallization from 50% aqueous ethanol to give 3-[2-{2-(carboxymethylamino)ethyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.50 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between water and ethyl acetate
  3. customThe aqueous layer was separated
  4. customto give the precipitate, which
  5. customwas collected
  6. custompurified by recrystallization from 50% aqueous ethanol

Sources & evidence

ORD record
ord-25f44224c957498b948adf14d5539cc1
Source dataset
uspto-grants-1994_08
Patent number
US05338743

Reaction notes

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