Cesium carbonate → 1-[4-({2-[(1S)-1-(2,3-dimethyl phenyl)ethyl]-1h-imidazol-1-yl}methyl)phenyl]-1h-1,2,4-triazole

HRID 734454Notes

Reaction equation

HRID 734454 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:9]([C:11]1[NH:12][CH:13]=[CH:14][N:15]=1)[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH:34]=[N:33][CH:32]=[N:31]2)=[CH:26][CH:25]=1>CN1CCCC1=O>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:9]([C:11]1[N:15]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([N:30]3[CH:34]=[N:33][CH:32]=[N:31]3)=[CH:28][CH:29]=2)[CH:14]=[CH:13][N:12]=1)[CH3:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27764891-(4-(bromomethyl)phenyl)-1H-1,2,4-triazoleHCID 24738933Demiditraz

Product 1

HCID 577184251-[4-({2-[(1S)-1-(2,3-dimethyl phenyl)ethyl]-1h-imidazol-1-yl}methyl)phenyl]-1h-1,2,4-triazoleYield 35.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a mixture of the compound of Example 58 (90 mg, 0.45 mmol) and caesium carbonate (244 mg, 0.75 mmol) in 1-methyl-2-pyrrolidinone (1 ml) was added 1-[4-(bromomethyl)phenyl]-1H-1,2,4-triazole (83 μl, 0.5 mmol). The reaction mixture was stirred at room temperature for 18 h and then concentrated in vacuo. The residue was dissolved in 1-methyl-2-pyrrolidinone (0.8 ml) and purified by automated preparative liquid chromatography (Gilson system, 150 mm×22.4 mm LUNA C18(2) 5 μm column, 20 ml/min) using an acetonitrile:water gradient [15:85 (3 min) to 98:2 (11 min)]. The appropriate fractions were combined and concentrated to give the title compound (57 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in 1-methyl-2-pyrrolidinone (0.8 ml)
  3. custompurified
  4. customwater gradient [15:85 (3 min) to 98:2 (11 min)]
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-66d3dacb87ed417a82f8b697a52b0705
Source dataset
uspto-grants-2009_09
Patent number
US07592362B2

Reaction notes

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