Hydrochloric Acid → HCID 58127756, compound

HRID 1257337Notes

Reaction equation

HRID 1257337 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]([C:13]2[N:14]=[C:15]([CH2:18][N:19]3[CH:23]=[C:22]([C:24]([O:26]CC)=[O:25])[CH:21]=[N:20]3)[S:16][CH:17]=2)[CH:10]=[CH:11][CH:12]=1)=[O:5].[OH-].[Na+].Cl>C(O)C.[Cl-].[Na+].O>[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]([C:13]2[N:14]=[C:15]([CH2:18][N:19]3[CH:23]=[C:22]([C:24]([OH:26])=[O:25])[CH:21]=[N:20]3)[S:16][CH:17]=2)[CH:10]=[CH:11][CH:12]=1)=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58127684ethyl 1-[(4-{3-[(methoxyacetyl)amino]phenyl}-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylate

Product 1

HCID 58127756HCID 58127756, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution (4 mL) of the compound (339 mg, 0.85 mmol) obtained in Example 26b in ethanol was added 2N aqueous sodium hydroxide solution (1.7 mL, 3.4 mmol), and the mixture was stirred at room temperature overnight. The reaction mixture was neutralized with 1N aqueous hydrochloric acid solution, saturated brine was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was recrystallized (ethyl acetate-hexane) to give the title compound (221 mg, 70%) as colorless crystals.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe resulting crude title compound was recrystallized (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-188362683c1f4260968eeb1080fc7960
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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