Hydrochloric Acid → [3-phenyl-1-[6-(2-phenyl-4-thiazolylmethoxy)-3-pyridylmethyl]-1H-pyrazol-4-yl]acetic acid

HRID 350297Notes

Reaction equation

HRID 350297 reaction equation
[C:1]1([C:7]2[C:11]([CH2:12][C:13]([O:15]CC)=[O:14])=[CH:10][N:9]([CH2:18][C:19]3[CH:20]=[N:21][C:22]([O:25][CH2:26][C:27]4[N:28]=[C:29]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[S:30][CH:31]=4)=[CH:23][CH:24]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[C:1]1([C:7]2[C:11]([CH2:12][C:13]([OH:15])=[O:14])=[CH:10][N:9]([CH2:18][C:19]3[CH:20]=[N:21][C:22]([O:25][CH2:26][C:27]4[N:28]=[C:29]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[S:30][CH:31]=4)=[CH:23][CH:24]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86760433ethyl [3-phenyl-1-(6-(2-phenyl-4-thiazolylmethoxy)-3-pyridylmethyl]-1H-pyrazol-4-yl]acetate

Product 1

HCID 69422951[3-phenyl-1-[6-(2-phenyl-4-thiazolylmethoxy)-3-pyridylmethyl]-1H-pyrazol-4-yl]acetic acidYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After a mixture of ethyl [3-phenyl-1-(6-(2-phenyl-4-thiazolylmethoxy)-3-pyridylmethyl]-1H-pyrazol-4-yl]acetate (536 mg), 1N sodium hydroxide solution (2 ml), tetrahydrofuran (4 ml), and ethanol (4 ml) was stirred at room temperature for 2 hours, 1N hydrochloric acid (2 ml) was added to the mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The resulting colorless crystals were collected by filtration to obtain [3-phenyl-1-[6-(2-phenyl-4-thiazolylmethoxy)-3-pyridylmethyl]-1H-pyrazol-4-yl]acetic acid (459 mg, yield: 91%). This was recrystallized from ethanol-hexane. Melting point: 118–119° C.

Workup

  1. extractionthe 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 resulting colorless crystals were collected by filtration

Sources & evidence

ORD record
ord-65b59db8415e49a5b3108ebee55f53ac
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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