Imidazole → HCID 58049391, compound

HRID 467965Notes

Reaction equation

HRID 467965 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][N:6]([CH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[C:7]([C:9]1[N:13]=[CH:12][N:11]([CH3:14])[N:10]=1)=[O:8].[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1.C(=O)([O-])[O-].[Cs+].[Cs+].NC1CCCCC1N>C(Cl)(Cl)Cl.[Cu](I)I.O1CCOCC1>[N:24]1([C:2]2[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=2)[CH2:5][N:6]([CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:7]([C:9]2[N:13]=[CH:12][N:11]([CH3:14])[N:10]=2)=[O:8])[CH:28]=[CH:27][N:26]=[CH:25]1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 46101,2-DiaminocyclohexaneHCID 10796Cesium carbonateHCID 58049421HCID 58049421, compound

Product 1

HCID 58049391HCID 58049391, compoundYield 19.8%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N-(3-iodobenzyl)-1-methyl-N-(tetrahydro-2H-pyran-4-yl)-1H-1,2,4-triazole-3-carboxamide (100 mg), imidazole (38 mg), copper iodide (9 mg), cesium carbonate (321 mg), 1,2-diaminocyclohexane (23 μL) and dioxane (1 mL) was stirred overnight at 120° C. After being left to cool, the mixture was diluted with chloroform, and the chloroform layer was washed with 12% aqueous ammonia and saturated saline, and dried over anhydrous magnesium sulfate. After filtering off the desiccant, the solvents were distilled off under reduced pressure and the resulting residue was purified by column chromatography (NH silica gel cartridge; hexane, ethyl acetate, chloroform/methanol=100:0 to 90:10) to give the titled compound (17 mg).

Workup

  1. waitAfter being left
  2. temperatureto cool
  3. washthe chloroform layer was washed with 12% aqueous ammonia and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtering off the desiccant
  6. distillationthe solvents were distilled off under reduced pressure
  7. customthe resulting residue was purified by column chromatography (NH silica gel cartridge; hexane, ethyl acetate, chloroform/methanol=100:0 to 90:10)

Sources & evidence

ORD record
ord-a04134b9593f4a79b3d681b1f8f4ce05
Source dataset
uspto-grants-2014_01
Patent number
US08623898B2

Reaction notes

Loading…