Hydrochloric Acid → 3-[3-phenyl-1-[3-(3-pyridylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionic acid

HRID 350147Notes

Reaction equation

HRID 350147 reaction equation
[C:1]1([C:7]2[C:11]([CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])=[CH:10][N:9]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([NH:28][C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)=[O:27])[CH:21]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].C(O)C.Cl>O1CCCC1>[C:1]1([C:7]2[C:11]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:10][N:9]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([NH:28][C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)=[O:27])[CH:21]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 23024973ethyl 3-[3-phenyl-1-[3-(3-pyridylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionate

Product 1

HCID 694259153-[3-phenyl-1-[3-(3-pyridylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionic acidYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 3-[3-phenyl-1-[3-(3-pyridylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionate (230 mg), 1 N aqueous sodium hydroxide solution (1.2 ml), ethanol (2 ml), and tetrahydrofuran (2 ml) was stirred at room temperature for one hour. After 1 N hydrochloric acid (1.2 ml) was added to the reaction mixture, the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The obtained crystals were collected by filtration, and 3-[3-phenyl-1-[3-(3-pyridylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionic acid (190 mg, yield: 86%) was obtained. This was recrystallized from tetrahydrofuran-hexane. Melting point: 131–132° C.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. filtrationThe obtained crystals were collected by filtration

Sources & evidence

ORD record
ord-1e9c6f54c2c74584a4476e6a883476cf
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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