Diisopropylethylamine → 8-Trifluoromethoxy-2-oxo-2H-chromene-3-carboxylic acid (4'-Methoxy-biphenyl-3-yl)-amide

HRID 240054

Reaktionsgleichung

Reaktionsgleichung von HRID 240054
CCN(C(C)C)C(C)C.[F:10][C:11]([F:28])([F:27])[O:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[O:21][C:20](=[O:23])[C:19]([C:24]([OH:26])=O)=[CH:18]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:53][O:54][C:55]1[CH:60]=[CH:59][C:58]([C:61]2[CH:66]=[CH:65][CH:64]=[C:63]([NH2:67])[CH:62]=2)=[CH:57][CH:56]=1>CN(C=O)C>[CH3:53][O:54][C:55]1[CH:56]=[CH:57][C:58]([C:61]2[CH:66]=[CH:65][CH:64]=[C:63]([NH:67][C:24]([C:19]3[C:20](=[O:23])[O:21][C:22]4[C:17]([CH:18]=3)=[CH:16][CH:15]=[CH:14][C:13]=4[O:12][C:11]([F:10])([F:28])[F:27])=[O:26])[CH:62]=2)=[CH:59][CH:60]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 27595634'-Methoxy(1,1'-biphenyl)-3-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866503588-Trifluoromethoxy-3-carboxy-coumarin

Produkt 1

HCID 866503718-Trifluoromethoxy-2-oxo-2H-chromene-3-carboxylic acid (4'-Methoxy-biphenyl-3-yl)-amideAusbeute 55,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIEA (0.0144 mL, 0.083 mmol) was added to 8-trifluoromethoxy-3-carboxy-coumarin (0.021 g, 0.075 mmol) and HATU (0.032 g, 0.083 mmol) in 0.36 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 4′-Methoxy-biphenyl-3-ylamine (0.015 g, 0.075 mmol) was added and allowed to react overnight when a solid precipitated out of solution. The resulting precipitate was filtered, dried under suction, and finally dried overnight in vacuo to give 0.019 g of product in 55% yield: LCMS (ESI) m/z 456 (MH+).

Aufarbeitung

  1. customresulted
  2. customto react overnight when a solid
  3. customprecipitated out of solution
  4. filtrationThe resulting precipitate was filtered
  5. customdried under suction, and finally dried overnight in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4cfa2ae74b664fce945c82dfd71906e8
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642788B2

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