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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
Notes
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Reaction equation

HRID 517227 reaction equation
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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-76aa9d9e84ca45ed8d9dca1dc1c8ce17
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09115093B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes