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

HRID 240050

Reaktionsgleichung

Reaktionsgleichung von HRID 240050
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.[CH2:53]([O:55][C:56]1[C:61]([C:62]2[CH:63]=[C:64]([NH2:68])[CH:65]=[CH:66][CH:67]=2)=[CH:60][CH:59]=[CH:58][N:57]=1)[CH3:54]>CN(C=O)C>[CH2:53]([O:55][C:56]1[C:61]([C:62]2[CH:63]=[C:64]([NH:68][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:65]=[CH:66][CH:67]=2)=[CH:60][CH:59]=[CH:58][N:57]=1)[CH3:54]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 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)-phenylamineHCID 866503588-Trifluoromethoxy-3-carboxy-coumarin

Produkt 1

HCID 441975218-Trifluoromethoxy-2-oxo-2H-chromene-3-carboxylic acid [3-(2-ethoxy-pyridin-3-yl)-phenyl]-amideAusbeute 48,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIEA (0.013 mL, 0.077 mmol) was added to 8-trifluoromethoxy-3-carboxy-coumarin (0.019 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 0.016 g of product in 48% yield: LCMS (ESI) m/z 471 (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-b5574170bc3d411d9e0780c827c7ecdc
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642788B2

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