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 1772449노트

반응식

HRID 1772449 반응식
[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]

참가 물질

9

반응물 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

생성물 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]urea수율 35%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-8a24a3b1fffd46babd1c91b800dc932d
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249133B2

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