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 517178ノート

反応式

HRID 517178 の反応式
[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

参加物

4

反応物 2

HCID 6147225,5-Dimethyl-3-{[3-(trifluoromethyl)phenyl]amino}cyclohex-2-en-1-one2 回HCID 116874181-Bromo-4-(chloro(isocyanato)methyl)benzene

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-329f82c7d1744fc286d56cf83eba67da
出典データセット
uspto-grants-2015_08
特許番号
US09115093B2

反応ノート

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