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

HRID 2074074Notes

Reaction equation

HRID 2074074 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 are suspended in 5 ml of ethanol and 12 ml of tetrahydrofuran. With ice cooling, 2 ml (25 mmol) of a 50% aqueous sodium hydroxide solution are added. The reaction mixture is stirred at room temperature overnight and then, with ice cooling, 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. extractionThe solution is extracted with dichloromethane
  2. concentrationThe organic phase is concentrated in vacuo
  3. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-02e97cd3a4774f0d8d4ab9b568f8c9b6
Source dataset
uspto-grants-2011_04
Patent number
US07919489B2

Reaction notes

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