Sodium Hydroxide → 3-Cyclopropyl-5-(6-hydroxy-pyridin-3-yl)-2-(4-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid

HRID 545345Notes

Reaction equation

HRID 545345 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH:29]2[CH2:31][CH2:30]2)[C:8]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=2)=[N:9][C:10]=1[C:11]1[CH:12]=[N:13][C:14]([OH:17])=[CH:15][CH:16]=1)=[O:5])C.[OH-].[Na+]>CCO>[CH:29]1([N:7]2[C:6]([C:4]([OH:5])=[O:3])=[C:10]([C:11]3[CH:12]=[N:13][C:14]([OH:17])=[CH:15][CH:16]=3)[N:9]=[C:8]2[C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:27])([F:28])[F:26])=[CH:20][CH:19]=2)[CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178468520HCID 178468520, compound

Product 1

HCID 1785240453-Cyclopropyl-5-(6-hydroxy-pyridin-3-yl)-2-(4-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acidYield 95.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 0.8 g (1.8 mmol) of 3-cyclopropyl-5-(6-hydroxy-pyridin-3-yl)-2-(4-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid ethyl ester in 3 ml of EtOH was added 0.6 ml of 6 M sodium hydroxide solution (3.8 mmol) and the mixture was heated to reflux for 16 h. The solvent was then evaporated, 1M hydrochloric acid solution was added and the resulting precipitate was isolated by filtration, affording 0.7 g (94%) of the title compound as a white solid. MS: 406.1 (MH+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 16 h
  3. customThe solvent was then evaporated
  4. addition1M hydrochloric acid solution was added
  5. customthe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-45b47bf50a6c4deba14b42ec4a0b4789
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

Loading…