2-Hydroxy benzimidazole → HCID 66650118, compound

HRID 418393Notes

Reaction equation

HRID 418393 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 MS (M+H)=450.

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-dd46705fc52845b2aa67d7c33489743b
Source dataset
uspto-grants-2012_01
Patent number
US08093275B2

Reaction notes

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