Water → 4-(2,5-Dioxo-1-(3-(trifluoromethyl)phenyl)-7-(4-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)benzonitrile

HRID 517233ノート

反応式

HRID 517233 の反応式
CC(C)([O-])C.[Na+].[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:30]2[C:35](=O)[CH2:34][CH:33]([C:37]3[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=3)[CH2:32][C:31]=2[O:47]CC)[NH:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=O)=[CH:11][CH:10]=1)#[N:8].[OH2:50]>C(#N)C>[O:50]=[C:17]1[NH:16][CH:15]([C:12]2[CH:13]=[CH:14][C:9]([C:7]#[N:8])=[CH:10][CH:11]=2)[C:30]2[C:31](=[O:47])[CH2:32][CH:33]([C:37]3[CH:38]=[CH:39][C:40]([C:43]([F:44])([F:46])[F:45])=[CH:41][CH:42]=3)[CH2:34][C:35]=2[N:19]1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:27])[F:28])[CH:21]=1

参加物

5

反応物 3

HCID 962WaterHCID 23676156Sodium t-butoxideHCID 86732305HCID 86732305、化合物2 回

生成物 1

HCID 867323544-(2,5-Dioxo-1-(3-(trifluoromethyl)phenyl)-7-(4-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)benzonitrile

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Sodium tert-butoxide (211 mg, 2.19 mmol) is added to a solution of 1-((4-cyanophenyl)-(2-ethoxy-6-oxo-4-(4-(trifluoromethyl)phenyl)cyclohex-1-enyl)methyl)-3-(3-(trifluorometh yl)phenyl)urea (intermediate 17, 825 mg, 1.37 mmol) in acetonitrile (12 mL) and the mixture is stirred at room temperature over night. Water is added and the mixture is extracted with ethyl acetate. The organic layer is dried over Na2SO4 and concentrated under reduced pressure. The residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 100:0 to 0:100). Yield: 135 mg; ESI mass spectrum [M+H]+=556, Retention time HPLC: 1.27 min, 1.29 min (1:1 mixture of diastereomers) (V011_S01).

後処理

  1. extractionthe mixture is extracted with ethyl acetate
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 100:0 to 0:100)
  5. additionESI mass spectrum [M+H]+=556, Retention time HPLC: 1.27 min, 1.29 min (1:1 mixture of diastereomers) (V011_S01)

出典と根拠

ORDレコード
ord-52254790f19b47cd9c27a94f7fa70827
出典データセット
uspto-grants-2015_08
特許番号
US09115093B2

反応ノート

読み込み中…