1-Phenyl-1,2-propanedione → HCID 69035433, Verbindung

HRID 1355364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1355364
[C:1]1([C:7](=O)[C:8](=O)[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:12][CH:13]([C:17]([NH2:19])=[O:18])[C:14]([NH2:16])=[O:15]>>[CH3:9][C:8]1[NH:16][C:14](=[O:15])[C:13]([C:17]([NH2:19])=[O:18])=[N:12][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

3

Edukt 2

HCID 113631-Phenyl-1,2-propanedioneHCID 964572-Aminopropanediamide

Produkt 1

HCID 69035433HCID 69035433, Verbindung

Versuchsvorschrift

In analogy to the procedure described in example 12 1-phenyl-1,2-propanedione and 2-aminomalonamide were heated in an aqueous solution to give 5-methyl-3-oxo-6-phenyl-3,4 -dihydro-pyrazine-2-carboxylic acid amide. Then, the 5-methyl-3-oxo-6-phenyl-3,4-dihydro-pyrazine-2-carboxylic acid amide was treated with triethylamine and phosphorus pentachloride in phosphorus oxychloride at reflux to give the 3-chloro-5-methyl-6-phenyl-pyrazine-2-carbonitrile. The 3-chloro-5-methyl-6-phenyl-pyrazine-2-carbonitrile was finally treated with 2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride (J. Heterocycl. Chem. 1971, 8(5), 779-83) and N-ethyldiisopropylamine in N,N-dimethylformamide at room temperature to yield the 5-methyl-6-phenyl-3-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-pyrazine-2-carbonitrile as yellow amorphous solid; MS: 341 (M+H)+.

Aufarbeitung

  1. temperaturewere heated in an aqueous solution

Quellen und Nachweise

ORD-Eintrag
ord-116d6420f1824b1d9549a93513b69de6
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586422B2

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