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

HRID 517235ノート

反応式

HRID 517235 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:36])[CH2:34][CH:33]([C:37]3[S:38][CH:39]=[CH:40][CH:41]=3)[CH2:32][C:31]=2OCC)[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:35](=[O:36])[CH2:34][CH:33]([C:37]3[S:38][CH:39]=[CH:40][CH:41]=3)[CH2:32][C:31]=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 867323091-((4-Cyanophenyl)-(2-ethoxy-6-oxo-4-(thiophen-2-yl)cyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)-urea2 回

生成物 1

HCID 867323564-(2,5-Dioxo-7-(thiophen-2-yl)-1-(3-(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 (108 mg, 1.13 mmol) is added to a solution of 1-((4-cyanophenyl)-(2-ethoxy-6-oxo-4-(thiophen-2-yl)cyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)-urea (intermediate 21, 507 mg, 0.94 mmol) in acetonitrile (6 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 two times by reversed phase HPLC (first purification: Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA; second purification: Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3). Yield: 31 mg; ESI mass spectrum [M+H]+=494, Retention time HPLC: 1.18 min, 1.20 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 two times
  5. customby reversed phase HPLC (first purification: Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA; second purification: Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3)
  6. additionESI mass spectrum [M+H]+=494, Retention time HPLC: 1.18 min, 1.20 min (1:1 mixture of diastereomers) (V011_S01)

出典と根拠

ORDレコード
ord-48a5466c73fe4753b77ce38b55b8d276
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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