Acetonitrile → (1Z)-1-[4-oxo-3-(2-propan-2-ylphenyl)-1,3-thiazolidin-2-ylidene]-3-[(E)-2-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]prop-1-enyl]urea

HRID 573830ノート

反応式

HRID 573830 の反応式
[F:1][C:2]([F:30])([F:29])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18](/[C:21](/[CH3:28])=C/C(N=[N+]=[N-])=O)=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[CH:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[NH:40][C:41]([NH2:43])=[S:42])([CH3:33])[CH3:32].[C:44](=[O:47])([O-])[O-].[Cs+].[Cs+].[C:50]([O-:53])(=O)[CH3:51].[Na+].BrCC(OC)=O.[C:61](#[N:63])C>C(OCC)(=O)C.C(O)C>[CH:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[N:40]1[C:50](=[O:53])[CH2:51][S:42]/[C:41]/1=[N:43]\[C:44]([NH:63]/[CH:61]=[C:21](/[C:18]1[CH:19]=[CH:20][C:15]([C:12]2[N:13]=[CH:14][N:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:30])[F:29])=[CH:5][CH:6]=3)[N:11]=2)=[CH:16][CH:17]=1)\[CH3:28])=[O:47])([CH3:33])[CH3:32]

参加物

9

反応物 6

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 517045Sodium AcetateHCID 2759507(2-(Propan-2-yl)phenyl)thioureaHCID 90404286(E)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)but-2-enoyl azide

生成物 1

HCID 90406458(1Z)-1-[4-oxo-3-(2-propan-2-ylphenyl)-1,3-thiazolidin-2-ylidene]-3-[(E)-2-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]prop-1-enyl]urea収率 37%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

(E)-3-(4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)but-2-enoyl azide (C29) (0.28 g, 0.68 mmol) in acetonitrile (3.4 mL) was heated at 80° C. for 3 hours. The reaction was cooled and 1-(2-isopropylphenyl)thiourea (0.14 g, 0.74 mmol) and cesium carbonate (0.28 g, 0.86 mmol) were added. The reaction was stirred at room temperature overnight, diluted with ethyl acetate and washed with water. The organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to provide an orange foam. To the crude material (0.39 g) was added sodium acetate (0.082 g, 1.0 mmol), ethanol (3.4 mL), and methyl 2-bromoacetate (0.10 mL, 1.0 mmol). The reaction mixture was heated at 65° C. for 3 hours. The reaction was cooled, diluted with ethyl acetate, and washed with water. The organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated. The crude compound was loaded onto a Celite® cartridge with dichloromethane and purified by flash column chromatography using 0-100% ethyl acetate/B, where B=1:1 dichloromethane/hexanes, as eluent to afford the title compound as an orange sticky gum (0.16 g, 37%).

後処理

  1. temperatureThe reaction was cooled
  2. washwashed with water
  3. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide an orange foam
  7. temperatureThe reaction mixture was heated at 65° C. for 3 hours
  8. temperatureThe reaction was cooled
  9. washwashed with water
  10. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. custompurified by flash column chromatography

出典と根拠

ORDレコード
ord-b0f0f544fefe4600a34086f2cda66d36
出典データセット
uspto-grants-2015_05
特許番号
US09029560B2

反応ノート

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