Diisopropylethylamine → 8-Methoxy-2-oxo-2H-chromene-3-carboxylic acid [3-(2-ethoxy-pyridin-3-yl)-phenyl]-amide

HRID 240049

Reaktionsgleichung

Reaktionsgleichung von HRID 240049
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.[CH2:50]([O:52][C:53]1[C:58]([C:59]2[CH:60]=[C:61]([NH2:65])[CH:62]=[CH:63][CH:64]=2)=[CH:57][CH:56]=[CH:55][N:54]=1)[CH3:51]>CN(C=O)C>[CH2:50]([O:52][C:53]1[C:58]([C:59]2[CH:60]=[C:61]([NH:65][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:62]=[CH:63][CH:64]=2)=[CH:57][CH:56]=[CH:55][N:54]=1)[CH3:51]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2345628-Methoxy-2-oxo-2H-chromene-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668651703-(2-Ethoxy-pyridin-3-yl)-phenylamine

Produkt 1

HCID 866503708-Methoxy-2-oxo-2H-chromene-3-carboxylic acid [3-(2-ethoxy-pyridin-3-yl)-phenyl]-amideAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIEA (0.013 mL, 0.077 mmol) was added to 8-methoxy-3-carboxy-coumarin (0.015 g, 0.070 mmol) and HATU (0.029 g, 0.077 mmol) in 0.36 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-(2-Ethoxy-pyridin-3-yl)-phenylamine (0.015 g, 0.070 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 0.025 g of product in 86% yield: LCMS (ESI) m/z 417 (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-8b2816b36661451a89c15a31c81c8b1d
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642788B2

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