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

HRID 1717374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1717374
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([NH:29][CH2:30][CH3:31])=[O:28])=[CH:23][CH:22]=3)[C:11]=2[CH2:12]P(OCC)(OCC)=O)=[O:6])[CH2:3][CH2:2]1.[H-].[Na+].[CH3:34][C:35]1[O:36][CH:37]=[C:38]([CH:40]=O)[N:39]=1.O>C1COCC1>[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([NH:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:26]=3)[C:11]=2/[CH:12]=[CH:40]/[C:38]2[N:39]=[C:35]([CH3:34])[O:36][CH:37]=2)=[O:6])[CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 110733722-Methyl-1,3-oxazole-4-carbaldehydeHCID 86629812N-cyclopropyl-5-(diethylphosphonomethyl)-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide

Produkt 1

HCID 57665228N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(E)-2-(2-methyl-1,3-oxazol-4-yl)vinyl]-1H-1,2,3-triazole-4-carboxamideAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of N-cyclopropyl-5-(diethylphosphonomethyl)-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide (500 mg) obtained in Example 321b) in THF (20 ml) was added sodium hydride (50% oil dispersion, 80 mg) at 0° C., and the mixture was stirred at room temperature for 1 hr. A solution of 2-methyl-1,3-oxazole-4-carbaldehyde (148 mg) in THF (5 ml) was added to the obtained reaction mixture, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated under reduced pressure, and the obtained residue was purified by silica gel column (ethyl acetate to ethyl acetate/methanol=4/1) to give the title compound as a white powder (380 mg).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe obtained residue was purified by silica gel column (ethyl acetate to ethyl acetate/methanol=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-920c2c5bff2448d8adc158f88a36a829
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803822B2

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