1-ethyl-4-hydrazino-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, ethyl ester → 8-Ethyl-4H-pyrazolo[4',3':5,6]pyrido[3,4-e][1,2,4]-triazolo[1,5-a]pyrimidin-5(8H)-one

HRID 1704755

Reaktionsgleichung

Reaktionsgleichung von HRID 1704755
[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:14]([O:16]CC)=O)[C:11]([NH:12][NH2:13])=[C:6]2[CH:5]=[N:4]1)[CH3:2].C(O[CH:22]=[N:23][C:24]#[N:25])C>O1CCOCC1>[CH2:1]([N:3]1[C:7]2[N:8]=[CH:9][C:10]3[C:14](=[O:16])[NH:25][C:24]4[N:12]([N:13]=[CH:22][N:23]=4)[C:11]=3[C:6]=2[CH:5]=[N:4]1)[CH3:2]

Komponenten

4

Edukt 2

HCID 1623571-ethyl-4-hydrazino-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, ethyl esterHCID 9920370Methanimidic acid, N-cyano-, ethyl ester

Produkt 1

HCID 1355938528-Ethyl-4H-pyrazolo[4',3':5,6]pyrido[3,4-e][1,2,4]-triazolo[1,5-a]pyrimidin-5(8H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

249 g. of 1-ethyl-4-hydrazino-1H-pyrazolo[3,4-b]-pyridine-5-carboxylic acid, ethyl ester (1 mol.) are refluxed in 1.5 liters of dry dioxane together with 98 g. of ethoxymethylene cyanamide for 12 hours. After cooling to room temperature, the precipitated 8-ethyl-4H-pyrazolo[4',3':5,6]pyrido[3,4-e][1,2,4]triazolo[1,5-a]-pyrimidin-5(8H)-one is filtered off and recrystallized from dimethylformanide, yield 135 g. (53%); m.p. 355°-356°.

Aufarbeitung

  1. filtrationthe precipitated 8-ethyl-4H-pyrazolo[4',3':5,6]pyrido[3,4-e][1,2,4]triazolo[1,5-a]-pyrimidin-5(8H)-one is filtered off
  2. customrecrystallized from dimethylformanide, yield 135 g

Quellen und Nachweise

ORD-Eintrag
ord-c2f4d14374094373aec83390d6410216
Quelldatensatz
uspto-grants-1978_11
Patentnummer
US04127655

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