Cesium carbonate → 1-(2-isopropylphenyl)-3-(3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propyl)urea

HRID 62072

Reaktionsgleichung

Reaktionsgleichung von HRID 62072
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[N-:28]=[C:29]=[O:30].[F:31][C:32]([F:56])([F:55])[O:33][C:34]1[CH:39]=[CH:38][C:37]([N:40]2[CH:44]=[N:43][C:42]([C:45]3[CH:50]=[CH:49][C:48]([CH2:51][CH2:52][CH2:53]N)=[CH:47][CH:46]=3)=[N:41]2)=[CH:36][CH:35]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>ClCCl.O.C(#N)C>[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][C:29]([NH:28][CH2:53][CH2:52][CH2:51][C:48]1[CH:47]=[CH:46][C:45]([C:42]2[N:43]=[CH:44][N:40]([C:37]3[CH:38]=[CH:39][C:34]([O:33][C:32]([F:56])([F:31])[F:55])=[CH:35][CH:36]=3)[N:41]=2)=[CH:50][CH:49]=1)=[O:30])([CH3:3])[CH3:2]

Komponenten

10

Edukt 6

HCID 10796Cesium carbonateHCID 125612-IsopropylanilineHCID 94429TriphosgeneHCID 105034IsocyanateHCID 516892Sodium BicarbonateHCID 904042683-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-1-amine

Produkt 1

HCID 1186750951-(2-isopropylphenyl)-3-(3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propyl)ureaAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To 2-isopropylaniline (0.50 g, 3.7 mmol) and sodium bicarbonate (0.93 g, 11 mmol) in dichloromethane and water (36 mL, 2:1) was added triphosgene (0.55 g, 1.9 mmol) at 0° C. The reaction was stirred until complete conversion to the isocyanate, as observed by thin layer chromatography. The reaction was then diluted with dichloromethane (100 mL), and the organic layer was separated from the water layer and concentrated. The residue obtained was dissolved in acetonitrile (15 mL) and 3-(4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-1-amine (1.2 g, 3.4 mmol) and cesium carbonate (1.1 g, 3.4 mmol) were added. The reaction was stirred at room temperature for 16 hours. The reaction was quenched with water (50 mL) and extracted with dichloromethane (3×100 mL). The organic layers were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography using high pressure liquid chromatography provided the title compound as an off-white solid (0.26 g, 16%).

Aufarbeitung

  1. customthe organic layer was separated from the water layer
  2. concentrationconcentrated
  3. customThe residue obtained
  4. customThe reaction was quenched with water (50 mL)
  5. extractionextracted with dichloromethane (3×100 mL)
  6. dry with materialThe organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-da2468c4aa91404388d54bd8211891cb
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09445594B2

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