Hydrochloric Acid → 1-Methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazole-2-carboxylic Acid

HRID 499912Notes

Reaction equation

HRID 499912 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)=[O:9])[N:4]=[C:3]1[C:22]([O:24]CC)=[O:23].[OH-].[Na+].Cl>C(O)C.O1CCCC1>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:19])([F:21])[F:20])=[CH:13][CH:12]=2)=[O:9])[N:4]=[C:3]1[C:22]([OH:24])=[O:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59421902Ethyl 1-methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazole-2-carboxylate

Product 1

HCID 594218021-Methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazole-2-carboxylic Acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

835 mg (2.13 mmol) of ethyl 1-methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazole-2-carboxylate (Example 28A) are suspended in 5 ml of ethanol and 12 ml of tetrahydrofuran. While cooling in ice, 2 ml (25 mmol) of 50% strength aqueous sodium hydroxide solution are added. The reaction mixture is stirred at room temperature overnight and then, while cooling in ice, acidified with 1N hydrochloric acid. The solution is extracted with dichloromethane. The organic phase is concentrated in vacuo. The residue is purified by preparative HPLC.

Workup

  1. temperatureWhile cooling in ice
  2. temperaturewhile cooling in ice
  3. extractionThe solution is extracted with dichloromethane
  4. concentrationThe organic phase is concentrated in vacuo
  5. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-5a2cdd0e81ca4f0dbdf6d1530973481b
Source dataset
uspto-grants-2010_08
Patent number
US07767704B2

Reaction notes

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