Hydrazine hydrate (1:1) → 4-(6-{1-[(Cyclopentylcarbonyl)amino]propyl}-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl)-benzamide

HRID 1791183Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1791183
Cl.[NH2:2][C:3](=[NH:13])[C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[O:9])=[CH:6][CH:5]=1.O.[NH2:15]N.[CH:17]1([C:22]([NH:24][CH:25]([CH2:33][CH3:34])[C:26](=O)[C:27](OCC)=[O:28])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18]1>C(O)C>[CH:17]1([C:22]([NH:24][CH:25]([C:26]2[C:27](=[O:28])[NH:13][C:3]([C:4]3[CH:5]=[CH:6][C:7]([C:8]([NH2:10])=[O:9])=[CH:11][CH:12]=3)=[N:2][N:15]=2)[CH2:33][CH3:34])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18]1

Komponenten

5

Edukt 3

HCID 24654Hydrazine hydrate (1:1)HCID 27242934-Amidinobenzamide HydrochlorideHCID 21991319Ethyl 3-[(cyclopentylcarbonyl)amino]-2-oxopentanoate

Produkt 1

HCID 1356820404-(6-{1-[(Cyclopentylcarbonyl)amino]propyl}-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl)-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2.84 g (14.2 mmol, 1 equiv.) 4-[amino(imino)methyl]benzamide hydrochloride are suspended in 10 ml of ethanol and 1.37 g (26.8 mmol, 1.2 equiv.) hydrazine hydrate are added. After stirring at 60° C. for 1 hour, 6.28 g (24.6 mmol, 1.1 equiv.) ethyl 3-[(cyclopentylcarbonyl)-amino]-2-oxopentanoate (Example 4A), dissolved in 40 ml of ethanol, are added. The reaction mixture is stirred at 70° C. (bath temperature) for 4 hours. The mixture is evaporated to dryness in vacuo and the product is purified by flash chromatography.

Aufarbeitung

  1. additionare added
  2. stirringThe reaction mixture is stirred at 70° C. (bath temperature) for 4 hours
  3. customThe mixture is evaporated to dryness in vacuo
  4. customthe product is purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d63c930ad8b54bf6bec77254a03a4189
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074790B2

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