Methanol → 7-(4-Chloro-phenyl)-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

HRID 277016Notes

Reaction equation

HRID 277016 reaction equation
[H-].[Na+].C1(S([CH2:12][C:13]2[N:17]=[C:16]([C:18]3[O:19][CH:20]=[CH:21][CH:22]=3)[NH:15][N:14]=2)(=O)=O)C=CC=CC=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]=[CH:31][C:32]#[N:33])=[CH:26][CH:25]=1.CO>O1CCCC1>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[CH:31]=[C:32]([NH2:33])[N:14]3[N:15]=[C:16]([C:18]4[O:19][CH:20]=[CH:21][CH:22]=4)[N:17]=[C:13]3[CH:12]=2)=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 342433-(4-Chlorophenyl)prop-2-enenitrileHCID 178527402HCID 178527402, compound

Product 1

HCID 99486227-(4-Chloro-phenyl)-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamineYield 36.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.7 g (0.015 mol) sodiumhydride (55%) were added to a solution of 1.50 g (0.005 mol) 3-benzenesulfonylmethyl-5-furan-2-yl-1H-[1,2,4]triazole in 50 ml tetrahydrofuran. The mixture was refluxed and 0.85 g (0.005 mol) 3-(4-chlorophenyl)-2-propenenitrile in 30 ml tetrahydrofuran were added during, aperiod of 5.5 hours. Boiling was continued for 30 minutes and then 20 ml methanol were added at room temperature. Evaporation of the solvent and chromatography on silicagel with dichloromethane/methanol 99/1 gave 0.57 g (35%) 7-(4-chloro-phenyl)-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine as pale crystals. MS m/e (%): 311 (M+H+, 100).

Workup

  1. temperatureThe mixture was refluxed
  2. customEvaporation of the solvent and chromatography on silicagel with dichloromethane/methanol 99/1

Sources & evidence

ORD record
ord-f9fd2eb9b4a441a6ac8439b2db64acec
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Reaction notes

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