Methanol → 2-Furan-2-yl-7-pyridin-4-yl-[1,2,4]triazolo [1,5-a]pyridin-5-ylamine

HRID 277011

Reaktionsgleichung

Reaktionsgleichung von HRID 277011
[H-].[Na+].C1(S([C:12]2[N:16]=[C:15]([C:17]3[O:18][CH:19]=[CH:20][CH:21]=3)[N:14](C)[N:13]=2)(=O)=O)C=CC=CC=1.[N:23]1[CH:28]=[CH:27][C:26]([CH:29]=[CH:30][C:31]#[N:32])=[CH:25][CH:24]=1.[CH3:33]O>O1CCCC1>[O:18]1[CH:19]=[CH:20][CH:21]=[C:17]1[C:15]1[N:16]=[C:12]2[CH:33]=[C:29]([C:26]3[CH:27]=[CH:28][N:23]=[CH:24][CH:25]=3)[CH:30]=[C:31]([NH2:32])[N:13]2[N:14]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 534078083-Pyridin-4-YL-acrylonitrileHCID 701702463-benzenesulfonyl-methyl-5-furan-2-yl-1H-[1,2,4]triazole

Produkt 1

HCID 98820812-Furan-2-yl-7-pyridin-4-yl-[1,2,4]triazolo [1,5-a]pyridin-5-ylamineAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a boiling suspension of 5.9 g(0.12 mol) sodiumhydride (55%) in 100 ml tetrahydrofuran was slowly added over a period of 6 hours a mixture of 10.1 g (0.035 mol) 3-benzenesulfonyl-methyl-5-furan-2-yl-1H-[1,2,4]triazole and 4.56 g (0.035 mol) 3-(4-pyridinyl)-2-propenenitrile in 400 ml tetrahydrofuran. Boiling was continued for 15 hours and then 50 ml methanol were added at room temperature. Evaporation of the solvent and chromatography on silicagel with dichloromethane/methanol 95/5 gave 1.3 g (13%) 2-furan-2-yl-7-pyridin-4-yl-[1,2,4]triazolo [1,5-a]pyridin-5-ylamine as yellow crystals with mp. 294-296° C.

Aufarbeitung

  1. additionwas slowly added over a period of 6 hours
  2. customEvaporation of the solvent and chromatography on silicagel with dichloromethane/methanol 95/5

Quellen und Nachweise

ORD-Eintrag
ord-c380808d2e1f4b5990ee50f4ac7eebb4
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355653B1

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