Water → 4-(4-Bromophenyl)-1-(3-(trifluoromethyl)phenyl)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-2,5-dione

HRID 927191노트

반응식

HRID 927191 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](Cl)[N:9]=[C:10]=[O:11])=[CH:4][CH:3]=1.[F:13][C:14]([F:29])([F:28])[C:15]1[CH:16]=[C:17]([NH:21][C:22]2[CH2:26][CH2:25][C:24](=[O:27])[CH:23]=2)[CH:18]=[CH:19][CH:20]=1.O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:9][C:10](=[O:11])[N:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:13])([F:28])[F:29])[CH:16]=3)[C:22]3[CH2:26][CH2:25][C:24](=[O:27])[C:23]2=3)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 116874181-Bromo-4-(chloro(isocyanato)methyl)benzeneHCID 903110573-[3-(Trifluoromethyl)anilino]cyclopent-2-en-1-one

생성물 1

HCID 903109024-(4-Bromophenyl)-1-(3-(trifluoromethyl)phenyl)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-2,5-dione

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 1-bromo-4-(chloro(isocyanato)methyl)benzene (14.7 g, 47.6 mmol) in dichloromethane (100 mL) is added to a solution of 3-(3-(trifluoromethyl)phenylamino)-cyclopent-2-enone (11.0 g, 45.6 mmol) in dichloromethane (100 mL) and the mixture is heated at reflux for 1.5 hours. Water is added, and the phases are extracted twice with dichloromethane. The combined organic layers are concentrated and the residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 4:1 to ethyl acetate). Yield: 7.5 g; ESI mass spectrum: ESI mass spectrum: [(79Br)-M+H]+=451, [(81Br)-M+H]+=453; Retention time HPLC: 1.15 min (V012_S01).

후처리

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 1.5 hours
  3. extractionthe phases are extracted twice with dichloromethane
  4. concentrationThe combined organic layers are concentrated
  5. customthe residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 4:1 to ethyl acetate)
  6. custom1.15 min (V012_S01)

출처 및 근거

ORD 기록
ord-7df1f7a3829c426980bb7df805e1562a
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290459B1

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