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

HRID 517234ノート

反応式

HRID 517234 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]=[C:41]([O:43][CH3:44])[C:40]([O:45][CH3:46])=[C:39]([O:47][CH3:48])[CH:38]=3)[CH2:32][C:31]=2[O:49]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:18])=[CH:11][CH:10]=1)#[N:8].O>C(#N)C>[O:18]=[C:17]1[NH:16][CH:15]([C:12]2[CH:11]=[CH:10][C:9]([C:7]#[N:8])=[CH:14][CH:13]=2)[C:30]2[C:31](=[O:49])[CH2:32][CH:33]([C:37]3[CH:38]=[C:39]([O:47][CH3:48])[C:40]([O:45][CH3:46])=[C:41]([O:43][CH3:44])[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:27])([F:28])[F:29])[CH:21]=1

参加物

5

反応物 3

HCID 962WaterHCID 23676156Sodium t-butoxideHCID 867323071-((4-Cyanophenyl)(2-ethoxy-6-oxo-4-(3,4,5-trimethoxyphenyl)cyclohex-1-enyl)-methyl)-3-(3-(trifluoromethyl)phenyl)urea2 回

生成物 1

HCID 867323554-(2,5-Dioxo-1-(3-(trifluoromethyl)phenyl)-7-(3,4,5-trimethoxyphenyl)-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 (126 mg, 1.32 mmol) is added to a solution of 1-((4-cyanophenyl)-(2-ethoxy-6-oxo-4-(3,4,5-trimethoxyphenyl)cyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea (intermediate 19, 684 mg, 1.10 mmol) in acetonitrile (8 mL) and the mixture is stirred at room temperature for 2 h. 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 reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 190 mg; ESI mass spectrum [M+H]+=578, Retention time HPLC: 1.13 min, 1.14 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 reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA)
  5. additionESI mass spectrum [M+H]+=578, Retention time HPLC: 1.13 min, 1.14 min (1:1 mixture of diastereomers) (V011_S01)

出典と根拠

ORDレコード
ord-8e99b40dd80b4c4bb7b3958341770aea
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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