Methyl iodide → HCID 86690472, compound

HRID 1026748Notes

Reaction equation

HRID 1026748 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([CH2:10][N:11]([CH:19]2[CH2:22][CH2:21][CH2:20]2)[C:12]([C:14]2[N:18]=[CH:17][NH:16][N:15]=2)=[O:13])[CH:7]=[CH:6][N:5]=1.CI.[C:25](=O)([O-])O.[Na+]>CN(C)C=O.O>[Br:3][C:4]1[CH:9]=[C:8]([CH2:10][N:11]([CH:19]2[CH2:22][CH2:21][CH2:20]2)[C:12]([C:14]2[N:18]=[CH:17][N:16]([CH3:25])[N:15]=2)=[O:13])[CH:7]=[CH:6][N:5]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 178520001HCID 178520001, compound

Product 1

HCID 86690472HCID 86690472, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (186 mg) was added to a solution of N-[(2-bromopyridin-4-yl)methyl]-N-cyclobutyl-1H-1,2,4-triazole-3-carboxamide (1.3 g) in dimethylformamide (10 mL), and the mixture was stirred at room temperature for 15 min. Methyl iodide (0.25 mL) was added thereto and the mixture was stirred at room temperature for 17.5 hr. Saturated aqueous sodium hydrogen carbonate solution and water were added to the reaction mixture, followed by extraction with ethyl acetate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=75:25-0:100) to afford the title compound (748 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 17.5 hr
  2. extractionfollowed by extraction with ethyl acetate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=75:25-0:100)

Sources & evidence

ORD record
ord-f1c671e87e794bb4b99ce86539f054b9
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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