Water → N-cyclopropyl-1-{4-[(ethylamino)carbonyl]-2-[(5-fluoropentyl)oxy]phenyl}-5-methyl-1H-1,2,3-triazole-4-carboxamide

HRID 1717347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1717347
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([NH:21][CH2:22][CH3:23])=[O:20])=[CH:15][C:14]=3[OH:24])[C:11]=2[CH3:12])=[O:6])[CH2:3][CH2:2]1.Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][F:31].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([NH:21][CH2:22][CH3:23])=[O:20])=[CH:15][C:14]=3[O:24][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][F:31])[C:11]=2[CH3:12])=[O:6])[CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 120236Pentane, 1-bromo-5-fluoro-HCID 57664949N-cyclopropyl-1-{4-[(ethylamino)carbonyl]-2-hydroxyphenyl}-5-methyl-1H-1,2,3-triazole-4-carboxamide

Produkt 1

HCID 57665126N-cyclopropyl-1-{4-[(ethylamino)carbonyl]-2-[(5-fluoropentyl)oxy]phenyl}-5-methyl-1H-1,2,3-triazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of N-cyclopropyl-1-{4-[(ethylamino)carbonyl]-2-hydroxyphenyl}-5-methyl-1H-1,2,3-triazole-4-carboxamide (0.17 g) obtained in Example 141 in DMF (5 ml) were added 1-bromo-5-fluoropentane (0.11 g) and potassium carbonate (0.07 g), and the mixture was stirred at 50° C. overnight. The reaction mixture was allowed to cool to room temperature, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate-hexane (2:1). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (ethyl acetate) to give the title compound as a pale-yellow amorphous substance (0.16 g, 77%).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate-hexane (2:1)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-32d58f975df942efbbc0b2658feecc5f
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803822B2

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