Water → 6-morpholin-4-yl-2-(2-trifluoromethyl-phenyl)-1H-benzoimidazole-4-carboxylic acid methyl ester

HRID 85140

Reaktionsgleichung

Reaktionsgleichung von HRID 85140
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:7]=[C:6]([NH2:16])[C:5]=1[NH2:17].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].O.[F:29][C:30]([F:40])([F:39])[C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH:33]=O>CCO>[CH3:1][O:2][C:3]([C:4]1[C:5]2[N:17]=[C:33]([C:32]3[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=3[C:30]([F:29])([F:39])[F:40])[NH:16][C:6]=2[CH:7]=[C:8]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[CH:9]=1)=[O:18]

Komponenten

6

Edukt 4

HCID 962WaterHCID 123067o-(Trifluoromethyl)benzaldehydeHCID 656671Sodium PyrosulfiteHCID 58279190Methyl 2,3-diamino-5-morpholinobenzoate

Produkt 1

HCID 672018076-morpholin-4-yl-2-(2-trifluoromethyl-phenyl)-1H-benzoimidazole-4-carboxylic acid methyl esterAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a mixture of 2,3-diamino-5-morpholin-4-yl-benzoic acid methyl ester (73; 600 mg, 2.39 mmol) in EtOH (60 ml) was added sodium metabisulfite (373 mg, 1.96 mmol), H2O (2 ml) and 2-trifluoromethylbenzaldehyde (74; 990 mg, 5.69 mmol). The resulting reaction mixture was stirred under reflux for 3 h. It was then cooled to room temperature and concentrated under reduced pressure. Purification by chromatography afforded 6-morpholin-4-yl-2-(2-trifluoromethyl-phenyl)-1H-benzoimidazole-4-carboxylic acid methyl ester 75 (670 mg, 69.2%) as a yellow solid.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperatureunder reflux for 3 h
  3. concentrationconcentrated under reduced pressure
  4. customPurification by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d741fbfb82864efe8cd33c080ddb010c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846947B2

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