5,5-Dimethyl-3-{[3-(trifluoromethyl)phenyl]amino}cyclohex-2-en-1-one → 4-(4-Bromophenyl)-7,7-dimethyl-1-(3-(trifluoromethyl)phenyl)-3,4,7,8-tetrahydroquinazoline-2,5(1H,6H)-dione

HRID 517178노트

반응식

HRID 517178 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.[CH3:13][C:14]1([CH3:32])[CH2:19][C:18](=[O:20])[CH:17]=[C:16]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH2:15]1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:18](=[O:20])[CH2:19][C:14]([CH3:32])([CH3:13])[CH2:15][C:16]=3[N:21]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:30])[F:31])[CH:23]=3)[C:10](=[O:11])[NH:9]2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 6147225,5-Dimethyl-3-{[3-(trifluoromethyl)phenyl]amino}cyclohex-2-en-1-one2회HCID 116874181-Bromo-4-(chloro(isocyanato)methyl)benzene

생성물 1

HCID 867322984-(4-Bromophenyl)-7,7-dimethyl-1-(3-(trifluoromethyl)phenyl)-3,4,7,8-tetrahydroquinazoline-2,5(1H,6H)-dione

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 1-bromo-4-(chloro(isocyanato)methyl)benzene (435 mg, 1.77 mmol) in dichloromethane (5 mL) is added to a solution of 5,5-dimethyl-3-(3-(trifluoromethyl)-phenylamino)cyclohex-2-enone (intermediate 8, 500 mg, 1.77 mmol) in dichloromethane (15 mL) and the mixture is heated at reflux over night. All volatiles are evaporated and the residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 90:10 to 60:40). Yield: 389 mg; ESI mass spectrum: [(79Br)-M+H]+=493, [(81Br)-M+H]+=495; Retention time HPLC: 1.38 min (Z002—002).

후처리

  1. temperaturethe mixture is heated
  2. temperatureat reflux over night
  3. customAll volatiles are evaporated
  4. customthe residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 90:10 to 60:40)
  5. custom1.38 min (Z002—002)

출처 및 근거

ORD 기록
ord-329f82c7d1744fc286d56cf83eba67da
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115093B2

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