1-Azido-2,3-dichlorobenzene → 5-(4-Chlorophenyl)-2-{[1-(2,3-dichlorophenyl)-1H-1,2,3-triazol-4-yl]methyl}-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714711ノート

反応式

HRID 714711 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:17][C@H:18]([OH:23])[C:19]([F:22])([F:21])[F:20])[C:10](=[O:16])[N:11]([CH2:13][C:14]#[CH:15])[N:12]=2)=[CH:4][CH:3]=1.[N:24]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=1[Cl:34])=[N+:25]=[N-:26]>C(#N)C.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:17][C@H:18]([OH:23])[C:19]([F:21])([F:22])[F:20])[C:10](=[O:16])[N:11]([CH2:13][C:14]3[N:26]=[N:25][N:24]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=4[Cl:34])[CH:15]=3)[N:12]=2)=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 126814021-Azido-2,3-dichlorobenzeneHCID 866909105-(4-Chlorophenyl)-2-(prop-2-yn-1-yl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

生成物 1

HCID 866909345-(4-Chlorophenyl)-2-{[1-(2,3-dichlorophenyl)-1H-1,2,3-triazol-4-yl]methyl}-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

試薬・触媒・溶媒 2

HCID 165397Cupric acetate monohydrate触媒HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

124 mg (0.36 mmol) of the compound from Example 14A were dissolved in 2 ml of acetonitrile, and 0.6 mg (0.003 mmol) of copper(II) acetate monohydrate and 56 mg (0.30 mmol) of 1-azido-2,3-dichlorobenzene were added. The mixture was stirred at 50° C. for 2 h. For work-up, the crude mixture was allowed to cool to RT and filtered through a little silica gel. The product was eluted with ethyl acetate and the solution obtained was concentrated under reduced pressure. The crude product was then purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:1). This gave 61 mg (31% of theory) of the target compound.

後処理

  1. temperatureto cool to RT
  2. filtrationfiltered through a little silica gel
  3. washThe product was eluted with ethyl acetate
  4. customthe solution obtained
  5. concentrationwas concentrated under reduced pressure
  6. customThe crude product was then purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:1)

出典と根拠

ORDレコード
ord-35728875fa3d49d8bb32f9a35f664351
出典データセット
uspto-grants-2015_11
特許番号
US09187466B2

反応ノート

読み込み中…