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Water → Methyl 2-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazolin-3(4H)-yl)propanoate

HRID 517227
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HRID 517227 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[O:7]=[C:8]1[NH:17][CH:16]([C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[C:15]2[C:14](=[O:26])[CH2:13][CH2:12][CH2:11][C:10]=2[N:9]1[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=1.Br[CH:38]([CH3:43])[C:39]([O:41][CH3:42])=[O:40].O>CN(C)C=O>[C:22]([C:21]1[CH:20]=[CH:19][C:18]([CH:16]2[C:15]3[C:14](=[O:26])[CH2:13][CH2:12][CH2:11][C:10]=3[N:9]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:34])[F:35])[CH:28]=3)[C:8](=[O:7])[N:17]2[CH:38]([CH3:43])[C:39]([O:41][CH3:42])=[O:40])=[CH:25][CH:24]=1)#[N:23]
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HCID 962WaterHCID 10796Cesium carbonateHCID 95576Methyl 2-bromopropionateHCID 867323264-(2,5-Dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-benzonitrile

생성물 1

HCID 86732348Methyl 2-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazolin-3(4H)-yl)propanoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

Cesium carbonate (713 mg, 2.19 mmol) is added to a solution of 4-(2,5-dioxo-1-(3-(trifluoromethyl)phenyl)1,2,3,4,5,6,7,8octahydroquinazolin-4-yl)-benzonitrile (example 1, 300 mg, 0.73 mmol) and methyl 2-bromopropanoate (244 mg, 1.46 mmol) in N,N-dimethylformamide (10 mL), and the mixture is stirred at 50° C. for 6 h and at room temperature over night. Water is added, and the mixture is extracted with dichloromethane. The organic layer is extracted with water and brine, dried over MgSO4 and concentrated under reduced pressure. Yield: 353 mg; ESI mass spectrum [M+H]+=498; Retention time HPLC: 0.97 min (Z018_S04).

후처리

  1. extractionthe mixture is extracted with dichloromethane
  2. extractionThe organic layer is extracted with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. custom0.97 min (Z018_S04)

출처 및 근거

ORD 기록
ord-76aa9d9e84ca45ed8d9dca1dc1c8ce17
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115093B2

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