Ethyl p-methylbenzenesulfonate → Ethyl-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-amine

HRID 277039

Reaction equation

HRID 277039 reaction equation
[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].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH2:25]([NH:15][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]

Participants

6

Reactant 4

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

Product 1

HCID 9904961Ethyl-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-amineYield 117.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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. 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 0.37 g(17%) ethyl-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-amine as beige crystals. MS m/e (%): 316 (M+H+, 100).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. customEvaporation of the solvent and chromatography on silicagel with dichloromethane/methanol 96/4

Sources & evidence

ORD record
ord-3dd85b7dcf324760a84d78e13f421c26
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Linked notes

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