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

HRID 491765ノート

反応式

HRID 491765 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-53a53a0a0dcc4c399b13c80204e6a00f
出典データセット
uspto-grants-2009_05
特許番号
US07531565B2

反応ノート

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