1-Hydroxybenzotriazole → HCID 86722023, compound

HRID 525003Notes

Reaction equation

HRID 525003 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([OH:8])=O.[F:9][C:10]1[CH:11]=[C:12]([CH:14]=[C:15]([F:17])[CH:16]=1)[NH2:13].C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[F:9][C:10]1[CH:11]=[C:12]([NH:13][C:6]([C:2]2[NH:1][CH:5]=[CH:4][N:3]=2)=[O:8])[CH:14]=[C:15]([F:17])[CH:16]=1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 965953,5-DifluoroanilineHCID 5743211H-Imidazole-2-carboxylic acid

Product 1

HCID 86722023HCID 86722023, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-imidazole-2-carboxylic acid (2.50 g, 22.3 mmol) in DMF (30 mL) were added 3,5-difluoroaniline (2.23 mL, 22.3 mmol), EDCHCl (6.41 g, 33.46 mmol) and HOBt (4.52 g, 33.46 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuum and the crude was dissolved in dichloromethane. The solution was washed with a diluted aqueous solution of potassium carbonate, dried over sodium sulphate, filtered and concentrated. 2.75 g (55% yield) of the title compound were obtained as a solid.

Workup

  1. customThe solvent was removed in vacuum
  2. dissolutionthe crude was dissolved in dichloromethane
  3. washThe solution was washed with a diluted aqueous solution of potassium carbonate
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bc976287e83d4aa2a8077d67f43f23d7
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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