Water → 3,6-diphenyl-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-1,2,3-triazolo[4,5-b]pyridine

HRID 1017629Notes

Reaction equation

HRID 1017629 reaction equation
[C:1]1([N:7]2[C:11]3[NH:12][C:13](=[O:22])[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:15][C:10]=3[N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:25][N:26]1[C:30]([CH2:31]Cl)=[N:29][CH:28]=[N:27]1.O>CN(C=O)C>[C:1]1([N:7]2[C:11]3=[N:12][C:13]([O:22][CH2:31][C:30]4[N:26]([CH3:25])[N:27]=[CH:28][N:29]=4)=[C:14]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:15]=[C:10]3[N:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 104192195-(Chloromethyl)-1-methyl-1H-1,2,4-triazoleHCID 1358341183,6-diphenyl-5-oxo-4H-1,2,3-triazolo[4,5-b]pyridine

Product 1

HCID 184040123,6-diphenyl-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-1,2,3-triazolo[4,5-b]pyridineYield 10.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 3,6-diphenyl-5-oxo-4H-1,2,3-triazolo[4,5-b]pyridine (0.03 g, 0.10 mmol) and sodium hydride (55% in oil, 0.006 g, 0.12 mmol) in dry DMF (2 ml) was stirred at room temperature under nitrogen until all effervescence had ceased. A solution of 2-methyl-3-chloromethyl-1,2,4-triazole (0.025 g, 0.20 mmol) in dry DMF (0.5 ml) was added and the mixture was stirred for 4 days. Water (20 ml) was added and the aqueous solution was extracted with 10% methanol-dichloromethane (20 ml). The extract was dried (Na2SO4), filtered and concentrated. Preparative thin-layer chromatography on silica gel, eluting with 5% methanol-dichloromethane, gave the alkylation product which was recrystallised from ethyl acetate-hexane to give 3,6-diphenyl-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-1,2,3-triazolo[4,5-b]pyridine (0.004 g, 10%) as a white, crystalline solid, m.p. 153-156° C. δH (360 MHz; CDCl3) 3.71 (3H, s), 5.69 (2H, s), 7.42-7.54 (6H, m), 7.63 (2H, dd, J=8 and 8), 7.86 (1H, s), 8.24 (2H, d, J=8) and 8.32 (1H, s); m/z (ES+) 383 (M+H+).

Workup

  1. stirringthe mixture was stirred for 4 days
  2. extractionthe aqueous solution was extracted with 10% methanol-dichloromethane (20 ml)
  3. dry with materialThe extract was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washPreparative thin-layer chromatography on silica gel, eluting with 5% methanol-dichloromethane
  7. customgave the alkylation product which
  8. customwas recrystallised from ethyl acetate-hexane

Sources & evidence

ORD record
ord-2f866ac33779411f80c4888e5316e977
Source dataset
uspto-grants-2002_11
Patent number
US06479506B1

Reaction notes

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