Hydrochloric Acid → HCID 69422754, compound

HRID 350132Notes

Reaction equation

HRID 350132 reaction equation
[CH3:1][N:2]([CH2:9][CH2:10][O:11][C:12]1[CH:36]=[CH:35][C:15]([CH2:16][N:17]2[CH:21]=[C:20]([CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])[C:19]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:18]2)=[CH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[OH-].[Na+].C(O)C.Cl>O1CCCC1>[CH3:1][N:2]([CH2:9][CH2:10][O:11][C:12]1[CH:36]=[CH:35][C:15]([CH2:16][N:17]2[CH:21]=[C:20]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])[C:19]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:18]2)=[CH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 69422253HCID 69422253, compound

Product 1

HCID 69422754HCID 69422754, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 3-[1-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzyl]-3-phenyl-1H-pyrazol-4-yl]propionate (750 mg), 1 N aqueous sodium hydroxide solution (3 ml), ethanol (3 ml), and tetrahydrofuran (3 ml) was stirred at room temperature for one hour. The reaction mixture was acidified with dilute hydrochloric acid, which 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-[1-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzyl]-3-phenyl-1H-pyrazol-4-yl]propionic acid (610 mg, yield: 90%) was obtained. This was recrystallized from ethyl acetate-hexane. Melting point: 110–111° C.

Workup

  1. extractionwas 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-c7b0fc212c4f402c8ceaf87b66737e08
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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