Hydrochloric Acid → HCID 66875666, compound

HRID 2381489Notes

Reaction equation

HRID 2381489 reaction equation
C[O:2][C:3](=[O:26])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([N:18]([CH3:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+].Cl>CO.O>[CH:6]1([CH2:5][CH:4]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([N:18]([CH3:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=[N:12]2)[C:3]([OH:26])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66875104HCID 66875104, compound

Product 1

HCID 66875666HCID 66875666, compoundYield 109.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-[4-(methyl-phenyl-amino)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl ester (66.3 mg, 0.18 mmol) in methanol (0.5 mL, 0.37M) was treated with a 4N aqueous sodium hydroxide solution (0.05 mL, 0.2 mmol) and was stirred at 25° C. overnight. After this time, the reaction was diluted with water (10 mL), acidified with a 1N aqueous hydrochloric acid solution and then was extracted into methylene chloride (3×25 mL). The combined organics were washed with a saturated aqueous sodium chloride solution (1×25 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to afford 3-cyclopentyl-2-[4-(methyl-phenyl-amino)-6-oxo-6H-pyridazin-1-yl]-propionic acid (67.3 mg) as a viscous, yellow oil. This material was used without further purification.

Workup

  1. extractionwas extracted into methylene chloride (3×25 mL)
  2. washThe combined organics were washed with a saturated aqueous sodium chloride solution (1×25 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f1e9d70ada6494caaa0e1a2e53bf0c7
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

Loading…