Triazabicyclodecene → 3-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid (tetrahydro-furan-3-yl)-amide

HRID 1920900

Reaktionsgleichung

Reaktionsgleichung von HRID 1920900
CO[C:3]([C:5]1[O:9][N:8]=[C:7]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:6]=1)=[O:4].[O:24]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25]1.N12CCCNC1=NCCC2>C1(C)C=CC=CC=1>[O:24]1[CH2:28][CH2:27][CH:26]([NH:29][C:3]([C:5]2[O:9][N:8]=[C:7]([O:10][CH2:11][C:12]3[C:13]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[N:14][O:15][C:16]=3[CH3:17])[CH:6]=2)=[O:4])[CH2:25]1

Komponenten

5

Edukt 3

HCID 79873TriazabicyclodeceneHCID 3365553Oxolan-3-amineHCID 67492296HCID 67492296, Verbindung

Produkt 1

HCID 468968873-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid (tetrahydro-furan-3-yl)-amideAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 3-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester (298 mg, 0.95 mmol) and tetrahydrofuran-3-ylamine (99 mg, 1.14 mmol) in toluene (1.5 mL) was added 1,5,7-triazabicyclo[4.4.0]dec-5-ene (40 mg, 0.28 mmol) and the reaction stirred under argon overnight at 50° C. Then the mixture was evaporated and the residue purified by chromatography (silica, heptane:ethyl acetate=4:1 to 1:1) to afford the title compound (87 mg, 25%) which was obtained as a colourless gum. MS: m/e=370.1 [M+H]+.

Aufarbeitung

  1. customThen the mixture was evaporated
  2. customthe residue purified by chromatography (silica, heptane:ethyl acetate=4:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-f347d3ddd85a421fbdaff4280efc8e30
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173652B2

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