Potassium tert-butoxide → 2-Phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

HRID 277033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 277033
CC(C)([O-])C.[K+].C1(S([CH2:16][C:17]2[N:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:19][N:18]=2)(=O)=O)C=CC=CC=1.[N:28]1[CH:33]=[CH:32][C:31]([CH:34]=[CH:35][C:36]#[N:37])=[CH:30][CH:29]=1>O1CCCC1>[C:22]1([C:20]2[N:21]=[C:17]3[CH:16]=[C:34]([C:31]4[CH:32]=[CH:33][N:28]=[CH:29][CH:30]=4)[CH:35]=[C:36]([NH2:37])[N:18]3[N:19]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Komponenten

5

Edukt 3

HCID 23665647Potassium tert-butoxideHCID 534078083-Pyridin-4-YL-acrylonitrileHCID 1785273983-benzenesulfonylmethyl-5-phenyl-1H-[1,2,4]triazole

Produkt 1

HCID 226297002-Phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamineAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a boiling suspension of 78.8 g(0.70 mol) potassium tert-butoxide in 400 ml tetrahydrofuran was slowly added over a period of 5 hours a mixture of 70.1 g (0.23 mol) 3-benzenesulfonylmethyl-5-phenyl-1H-[1,2,4]triazole and 30.5 g (0.23 mol) 3-(4-pyridinyl)-2-propenenitrile in 800 ml tetrahydrofuran. Boiling was continued for 18 hours and then the mixture was cooled to room temperature. Evaporation of the solvent and chromatography on silicael with dichloromethane/methanol 95/5 gave 19.8 g (29%) 2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine as yellow crystals with mp. 207-210° C., MS m/e (%):287 (M+, 100).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-374b2c8df40f49a69a8c1c6871518543
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355653B1

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