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

HRID 277011Notes

Reaction equation

HRID 277011 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-c380808d2e1f4b5990ee50f4ac7eebb4
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Reaction notes

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