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 927210ノート

反応式

HRID 927210 の反応式
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]

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-bfaef5c85ce34d43a02b31d8811a5c40
出典データセット
uspto-grants-2016_03
特許番号
US09290459B1

反応ノート

読み込み中…