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

HRID 2190145노트

반응식

HRID 2190145 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a7ce85e68c684580bc85b092a83f9487
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324268B2

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