Water → HCID 9842043, compound

HRID 1017628Notes

Reaction equation

HRID 1017628 reaction equation
[C:1]1([N:7]2[C:11]3[NH:12][C:13](=[O:20])[C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:15][C:10]=3[N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:23][N:24]1[C:28]([CH2:29]Cl)=[N:27][CH:26]=[N:25]1.O>CN(C=O)C>[C:1]1([N:7]2[C:11]3=[N:12][C:13]([O:20][CH2:29][C:28]4[N:24]([CH3:23])[N:25]=[CH:26][N:27]=4)=[C:14]([C:16]([O:18][CH3:19])=[O:17])[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 135834128HCID 135834128, compound

Product 1

HCID 9842043HCID 9842043, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 3-phenyl-5-oxo-6-methoxycarbonyl-4H-1,2,3-triazolo[4,5-b]pyridine (0.10 g, 0.37 mmol) and sodium hydride (55% in oil, 0.018 g, 0.40 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 (0.065 g, 0.50 mmol) in dry DMF (0.5 ml) was added and the mixture was stirred for 4 days. Water was added and the aqueous solution was extracted with dichloromethane. The extracts were dried (Na2SO4), filtered and concentrated. Preparative thin-layer chromatography on silica gel, eluting with 5% methanol-dichloromethane, gave the alkylation product which was washed with hot ethyl acetate to give 3-phenyl-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-6-methoxycarbonyl-1,2,3-triazolo[4,5-b]pyridine (0.036 g, 27%) as an off-white, crystalline solid, m.p. 188-190° C. Found: C, 55.97; H, 4.17; N, 26.93. C17H15N7O3 requires C, 55.89; H, 4.14; N, 26.84%. δH (360 MHz; CDCl3) 3.96 (3H, s), 4.08 (3H, s), 5.76 (2H, s), 7.50 (1H, t, J=7.5), 7.63 (2H, dd, J=7.5 and 7.5), 7.89 (1H, s), 8.23 (2H, d, J=7.5) and 8.96 (1H, s); m/z (ES+) 366 (M+H+).

Workup

  1. stirringthe mixture was stirred for 4 days
  2. extractionthe aqueous solution was extracted with dichloromethane
  3. dry with materialThe extracts were 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. washwas washed with hot ethyl acetate

Sources & evidence

ORD record
ord-64ea182ddd4b429a96e7581bd3465c98
Source dataset
uspto-grants-2002_11
Patent number
US06479506B1

Reaction notes

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