Water → 2-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridine-7-carboxylic acid ethyl ester

HRID 85143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 85143
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[C:10]([NH2:11])=[C:9]([NH2:12])[CH:8]=[N:7][CH:6]=1)[CH3:2].[F:14][C:15]([F:25])([F:24])[C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:5]1[C:10]2[N:11]=[C:18]([C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[C:15]([F:14])([F:24])[F:25])[NH:12][C:9]=2[CH:8]=[N:7][CH:6]=1)=[O:13])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 123067o-(Trifluoromethyl)benzaldehydeHCID 656671Sodium PyrosulfiteHCID 58278930Ethyl 4,5-diaminopyridine-3-carboxylate

Produkt 1

HCID 672030302-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridine-7-carboxylic acid ethyl esterAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture containing 4,5-diamino-nicotinic acid ethyl ester (79; 1.81 g, 10 mmol), 2-trifluoromethylbenzaldehyde (1.9 g, 11 mmol), Na2S2O5 (9.5 g, 50 mmol) in 50 mL of DMF was stirred at 120° C. for 18 h. Upon cooling to room temperature, the reaction mixture was poured into 100 mL of cold water. The resulting solids were collected by filtration, washed with water, and dried to provide 2-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridine-7-carboxylic acid ethyl ester 80 (2.35 g, 70%)

Aufarbeitung

  1. temperatureUpon cooling to room temperature
  2. filtrationThe resulting solids were collected by filtration
  3. washwashed with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-400243de709b4902953917502a47d376
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846947B2

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