2-Hydroxy benzimidazole → HCID 66650118, compound

HRID 2406895Notes

Reaction equation

HRID 2406895 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C@@H:7]([NH:9][C:10]([C:12]1[CH:13]=[C:14]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[CH:15]=[C:16](I)[CH:17]=1)=[O:11])[CH3:8].[NH:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[NH:28][C:27]1=[O:35].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CNC1CCCCC1NC>C1(C)C=CC=CC=1.[Cu]I>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C@@H:7]([NH:9][C:10]([C:12]1[CH:13]=[C:14]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[CH:15]=[C:16]([N:26]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[NH:28][C:27]2=[O:35])[CH:17]=1)=[O:11])[CH3:8]

Participants

7

Reactant 4

HCID 119852-Hydroxy benzimidazoleHCID 62657Potassium Phosphate, TribasicHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 66650112HCID 66650112, compound

Product 1

HCID 66650118HCID 66650118, compoundYield 17.8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

5-Iodo-4′-methyl-biphenyl-3-carboxylic acid ((S)-1-pyrazin-2-yl-ethyl)-amide (110 mg, 0.25 mmol) was dissolved in toluene (3 mL) and 1,3-dihydro-benzoimidazol-2-one (135 mg, 1.0 mmol), and CuI (15 mg), K3PO4 (212 mg, 1.0 mmol) and 1,2-bis(methylamino)cyclohexane (0.1 mL) were added. The reaction mixture was stirred at 110° C. overnight, then cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was separated and concentrated under reduced pressure and the residue was purified by preparative thin layer chromatography (7% methanol in dichloromethane) to give 20 mg (185 yield overall) of 4′-methyl-5-(2-oxo-2,3-dihydro-benzoimidazol-1-yl)-biphenyl-3-carboxylic acid ((S)-1-pyrazin-2-yl-ethyl)-amide

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by preparative thin layer chromatography (7% methanol in dichloromethane)

Sources & evidence

ORD record
ord-9191200bd0904c22abeca84de6129249
Source dataset
uspto-grants-2014_08
Patent number
US08809402B2

Reaction notes

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