Ethylenediamine → HCID 24752205, compound

HRID 2188815Notes

Reaction equation

HRID 2188815 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:16][C:11]=3[N:10]=[C:9]2[C:21]([F:24])([F:23])[F:22])=[N:6][CH:7]=1.[F:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:27]=1[C:28]([NH2:30])=[O:29].[O-]P([O-])([O-])=O.[K+].[K+].[K+].O.C(N)CN>O1CCOCC1.O.[Cu]I>[F:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:27]=1[C:28]([NH:30][C:2]1[N:3]=[CH:4][C:5]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:16][C:11]=3[N:10]=[C:9]2[C:21]([F:22])([F:24])[F:23])=[N:6][CH:7]=1)=[O:29]

Participants

8

Reactant 4

HCID 3301EthylenediamineHCID 874392,6-DifluorobenzamideHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 86646899HCID 86646899, compound

Product 1

HCID 24752205HCID 24752205, compoundYield 4.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Into a 50 mL 3-necked roundbottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of methyl 1-(5-bromopyrazin-2-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazole-5-carboxylate (xii) (200 mg, 0.50 mmol) in 1,4-dioxane (10 mL). To this was added 2,6-difluorobenzamide (235.5 mg, 1.50 mmol), followed by addition of K3PO4.H2O (500 mg, 1.48 mmol). CuI (11.7 mg, 0.06 mmol) was then added to the mixture, followed by ethane-1,2-diamine (EDA) (3.2 mg, 0.05 mmol). The resulting solution was allowed to stir for 45 minutes under reflux then diluted with 50 mL of H2O and extracted three times with 300 mL of EtOAc. The organic layers were combined then dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. The residue was purified by eluting through a silica gel column with a 1:10 EtOAc/PE solvent system to provide the final product methyl 1-(5-(2,6-difluorobenzamido)pyrazin-2-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazole-5-carboxylate (10 mg, 4% yield) as a white solid.

Workup

  1. customInto a 50 mL 3-necked roundbottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureunder reflux
  4. extractionextracted three times with 300 mL of EtOAc
  5. dry with materialThe organic layers were combined then dried over Na2SO4
  6. concentrationconcentrated by evaporation under vacuum
  7. customa rotary evaporator
  8. customThe residue was purified
  9. washby eluting through a silica gel column with a 1:10 EtOAc/PE solvent system

Sources & evidence

ORD record
ord-15c344ee4dc843dea5cc523b0d8b779b
Source dataset
uspto-grants-2012_12
Patent number
US08324219B2

Reaction notes

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