Triethylamine → 4-{[4,5-Bis(3-chlorophenyl)furan-2-yl]carbonyl}piperazin-2-one

HRID 2190145ノート

反応式

HRID 2190145 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([C:20](O)=[O:21])[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.C(N(CC)CC)C.[NH:34]1[CH2:39][CH2:38][NH:37][CH2:36][C:35]1=[O:40]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([C:20]([N:37]3[CH2:38][CH2:39][NH:34][C:35](=[O:40])[CH2:36]3)=[O:21])[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 231360Piperazin-2-oneHCID 580647634,5-Bis(3-chlorophenyl)furan-2-carboxylic acid

生成物 1

HCID 580647914-{[4,5-Bis(3-chlorophenyl)furan-2-yl]carbonyl}piperazin-2-one

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

600 mg (1.07 mmol) of the compound from Example 25A are provided in 14 ml of dry toluene, 0.24 ml (3.22 mmol) of thionyl chloride are added and the mixture is heated under reflux for 2.5 hours. The reaction mixture is concentrated, and the residue is taken up in 10 ml of dichloromethane and cooled to 0° C. 0.24 ml (1.72 mmol) of triethylamine and then 172 mg (1.72 mmol) of piperazin-2-one are then added, and the reaction mixture is stirred at RT overnight. The mixture is subsequently concentrated and the residue is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient). 302 mg (68% of theory) of the title compound are obtained.

後処理

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2.5 hours
  3. concentrationThe reaction mixture is concentrated
  4. concentrationThe mixture is subsequently concentrated
  5. customthe residue is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient)

出典と根拠

ORDレコード
ord-a7ce85e68c684580bc85b092a83f9487
出典データセット
uspto-grants-2012_12
特許番号
US08324268B2

反応ノート

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