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

HRID 2277416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2277416
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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1661679caa5c46de99a31372b2624242
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133165B2

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