Acetonitrile → (1Z)-1-[3-(5-methyl-2-propan-2-ylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]-3-[2-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]propyl]urea

HRID 573848ノート

反応式

HRID 573848 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]([CH:21]([CH3:28])[CH2:22]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][C:37]([CH3:40])=[CH:36][C:35]=1[NH:41][C:42]([NH2:44])=[S:43])([CH3:33])[CH3:32].[C:45](=[O:48])([O-])[O-].[Cs+].[Cs+].[C:51]([O-:54])(=O)[CH3:52].[Na+].BrCC(OC)=O.C(#[N:64])C>C(OCC)(=O)C.C(O)C>[CH:31]([C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][C:35]=1[N:41]1[C:51](=[O:54])[CH2:52][S:43]/[C:42]/1=[N:44]\[C:45]([NH:64][CH2:22][CH: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:29])([F:1])[F:30])=[CH:5][CH:6]=3)[N:11]=2)=[CH:16][CH:17]=1)[CH3:28])=[O:48])([CH3:33])[CH3:32]

参加物

9

反応物 6

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 517045Sodium AcetateHCID 893731681-(2-Isopropyl-5-methylphenyl)thioureaHCID 904042293-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)butanoyl azide

生成物 1

HCID 90404418(1Z)-1-[3-(5-methyl-2-propan-2-ylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]-3-[2-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]propyl]urea収率 35%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3-(4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)butanoyl azide (C42) (0.22 g, 0.52 mmol) in acetonitrile (2.6 mL) was heated at 80° C. for 2 hours. The reaction was cooled and 1-(2-isopropyl-5-methylphenyl)thiourea (0.12 g, 0.57 mmol) and cesium carbonate (0.20 g, 0.61 mmol) were added. The reaction was stirred at room temperature for 18 hours. Sodium acetate (0.093 g, 1.1 mmol), methyl 2-bromoacetate (0.07 mL, 0.78 mmol) and ethanol (2.6 mL) were added, and the reaction mixture was heated at 65° C. for 3 hours. The reaction was cooled, diluted with ethyl acetate, and washed with water. The aqueous layer was extracted once more with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was loaded onto a Celite® cartridge 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 solid (0.12 g, 35%).

後処理

  1. temperatureThe reaction was cooled
  2. temperaturethe reaction mixture was heated at 65° C. for 3 hours
  3. temperatureThe reaction was cooled
  4. washwashed with water
  5. extractionThe aqueous layer was extracted once more with ethyl acetate
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by flash column chromatography

出典と根拠

ORDレコード
ord-c51902fef0ed4af897249beea98ed236
出典データセット
uspto-grants-2015_05
特許番号
US09029560B2

反応ノート

読み込み中…