p-Toluenesulfonic acid → Diethyl-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-amine

HRID 277055

Reaktionsgleichung

Reaktionsgleichung von HRID 277055
[C:1]1([C:7]2[N:22]=[C:10]3[CH:11]=[C:12]([C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)[CH:13]=[C:14]([NH2:15])[N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:25](OS(C1C=CC(C)=CC=1)(=O)=O)[CH3:26].[CH3:38][C:39]1C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH2:25]([N:15]([CH2:38][CH3:39])[C:14]1[N:9]2[N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:22]=[C:10]2[CH:11]=[C:12]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH:13]=1)[CH3:26]

Komponenten

7

Edukt 5

HCID 6101p-Toluenesulfonic acidHCID 6638Ethyl p-methylbenzenesulfonateHCID 24758Sodium hydride2×HCID 516892Sodium BicarbonateHCID 226297002-Phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Produkt 1

HCID 9906109Diethyl-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-amineAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 0.29 g (0.001 mol) 2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine in 50 ml dimethylformamide was treated with 0.05 g (0.001 mol) sodiumhydride(55%) for 15 minutes at room temperature. Then 0.22 g (0.001 mol) ethyl-p-toluenesulfonate were added and stirring was continued for 22 hours. Addition of sodiumhydride and p-toluenesulfonate was repeated three times. After each addition stirring was continued at 50° C. for 20 hours. Saturated aqueous sodiumbicarbonate was added and the mixture was extracted with dichloromethane. Evaporation of the solvent and chromatography on silicagel with dichloromethane/methanol 96/4 gave 0.05 g (15%) diethyl-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-amine as yellow oil. MS m/e (%): 343 (M+, 59), 314 (100), 300 (73), 104 (51).

Aufarbeitung

  1. additionAfter each addition
  2. stirringstirring
  3. waitwas continued at 50° C. for 20 hours
  4. extractionthe mixture was extracted with dichloromethane
  5. customEvaporation of the solvent and chromatography on silicagel with dichloromethane/methanol 96/4

Quellen und Nachweise

ORD-Eintrag
ord-38f8a5076cc64aeeac9ae0163886b886
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355653B1

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