Water → Methyl 2-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)propanoate

HRID 927210노트

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HRID 927210 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[O:7]=[C:8]1[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[C:12]2[CH2:24][CH2:25][C:26](=[O:27])[C:11]=2[CH:10]([C:28]2[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=2)[NH:9]1.Br[CH:37]([CH3:42])[C:38]([O:40][CH3:41])=[O:39].O>CN(C)C=O>[C:32]([C:31]1[CH:30]=[CH:29][C:28]([CH:10]2[N:9]([CH:37]([CH3:42])[C:38]([O:40][CH3:41])=[O:39])[C:8](=[O:7])[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=3)[C:12]3[CH2:24][CH2:25][C:26](=[O:27])[C:11]2=3)=[CH:35][CH:34]=1)#[N:33]

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 95576Methyl 2-bromopropionateHCID 778447734-(2,5-Dioxo-1-(3-(trifluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]-pyrimidin-4-yl)benzonitrile

생성물 1

HCID 90311249Methyl 2-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)propanoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

Cesium carbonate (737 mg, 2.26 mmol) is added to a solution of 4-(2,5-dioxo-1-(3-(tri-fluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-4-yl)benzonitrile (example 1, 300 mg, 0.76 mmol) and methyl 2-bromopropionate (252 mg, 1.51 mmol) in N,N-dimethylformamide (10.0 mL), and the mixture is stirred at 50° C. over night. Water is added, and the mixture is extracted with dichloromethane. The organic layer is washed twice with water, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 160 mg; ESI mass spectrum: [M+H]+=484; Retention time HPLC: 0.85 min (Z018_S04).

후처리

  1. extractionthe mixture is extracted with dichloromethane
  2. washThe organic layer is washed twice with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA)
  6. custom0.85 min (Z018_S04)

출처 및 근거

ORD 기록
ord-bfaef5c85ce34d43a02b31d8811a5c40
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290459B1

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