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

HRID 2277416Notes

Reaction equation

HRID 2277416 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH3:26])[CH:8]=[C:9]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)=[O:13])[N:10]=1)=[O:5])C.[OH-].[Na+].Cl>C(O)C.O1CCCC1>[CH3:26][N:7]1[CH:8]=[C:9]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:23])([F:25])[F:24])=[CH:17][CH:16]=2)=[O:13])[N:10]=[C:6]1[C:4]([OH:5])=[O:3]

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 1-methyl-4-[({[4-(trifluoromethoxy)phenyl]-amino}carbonyl)amino]-1H-imidazole-2-carboxylic acid ethyl ester (Example 3A) is suspended in 5 ml of ethanol and 12 ml of tetrahydrofuran. While being cooled with ice, 2 ml (25 mmol) of 50% aqueous sodium hydroxide solution is added. The reaction mixture is stirred overnight at room temperature and then made acidic with 1N hydrochloric acid while being cooled with ice. The solution is extracted with dichloromethane. The organic phase is concentrated by evaporation in a vacuum. The residue is purified by preparative HPLC.

Workup

  1. additionis added
  2. temperaturewhile being cooled with ice
  3. extractionThe solution is extracted with dichloromethane
  4. concentrationThe organic phase is concentrated by evaporation in a vacuum
  5. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-1661679caa5c46de99a31372b2624242
Source dataset
uspto-grants-2015_09
Patent number
US09133165B2

Reaction notes

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