Triethylamine → 1-(4-Fluoro-phenyl)-4-methyl-2-oxo-imidazolidine-4-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide

HRID 491765Notes

Reaction equation

HRID 491765 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][C:11]([CH3:16])([C:13]([OH:15])=O)[NH:10][C:9]2=[O:17])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH2:24][C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([C:33]([F:36])([F:35])[F:34])[CH:26]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[C:29]([C:28]1[CH:31]=[CH:32][C:25]([NH:24][C:13]([C:11]2([CH3:16])[CH2:12][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:9](=[O:17])[NH:10]2)=[O:15])=[CH:26][C:27]=1[C:33]([F:34])([F:35])[F:36])#[N:30]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 5221704-Amino-2-(trifluoromethyl)benzonitrileHCID 441926221-(4-Fluorophenyl)-4-methyl-2-oxoimidazolidine-4-carboxylic acid

Product 1

HCID 116328381-(4-Fluoro-phenyl)-4-methyl-2-oxo-imidazolidine-4-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amideYield 54.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(4-fluoro-phenyl)-4-methyl-2-oxo-imidazolidine-4-carboxylic acid (120 mg, 0.50 mmol) in DCM (15 mL) was treated oxalyl chloride (0.09 mL, 1.03 mmol) and one drop of dry DMF. After stirring 1 hour at room temperature, the solvent was removed in vacuo. To this residue, a solution of 4-amino-2-(trifluoromethyl)benzonitrile (277 mg, 1.49 mmol) and triethylamine (0.28 mL, 2.01 mmol) in dry DCM (10 mL) was added. After stirring overnight at room temperature, the mixture was concentrated in vacuo and the residue purified by flash chromatography to afford the title compound as a tan solid (110 mg, 54%).

Workup

  1. customthe solvent was removed in vacuo
  2. stirringAfter stirring overnight at room temperature
  3. concentrationthe mixture was concentrated in vacuo
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-53a53a0a0dcc4c399b13c80204e6a00f
Source dataset
uspto-grants-2009_05
Patent number
US07531565B2

Reaction notes

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