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

HRID 240053

Reaktionsgleichung

Reaktionsgleichung von HRID 240053
CCN(C(C)C)C(C)C.[CH3:10][O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[O:20][C:19](=[O:22])[C:18]([C:23]([OH:25])=O)=[CH:17]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:50][O:51][C:52]1[CH:57]=[CH:56][C:55]([C:58]2[CH:63]=[CH:62][CH:61]=[C:60]([NH2:64])[CH:59]=2)=[CH:54][CH:53]=1>CN(C=O)C>[CH3:50][O:51][C:52]1[CH:53]=[CH:54][C:55]([C:58]2[CH:63]=[CH:62][CH:61]=[C:60]([NH:64][C:23]([C:18]3[C:19](=[O:22])[O:20][C:21]4[C:16]([CH:17]=3)=[CH:15][CH:14]=[CH:13][C:12]=4[O:11][CH3:10])=[O:25])[CH:59]=2)=[CH:56][CH:57]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2345628-Methoxy-2-oxo-2H-chromene-3-carboxylic acidHCID 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)

Produkt 1

HCID 441975238-Methoxy-2-oxo-2H-chromene-3-carboxylic acid (4'-Methoxy-biphenyl-3-yl)-amideAusbeute 69,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIEA (0.0144 mL, 0.083 mmol) was added to 8-methoxy-3-carboxy-coumarin (0.017 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 0.021 g of product in 68% yield: LCMS (ESI) m/z 402 (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-9b08cd0c9b3b4446abe2b6cc30e64b0c
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642788B2

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