Water → 6-Methyl-2-oxo-1-(3-trifluoromethylphenyl)-1,2-dihydro-pyridine-3-carboxylic acid (3-methyl-isoxazol-5-ylmethyl)-amide

HRID 559821

Reaktionsgleichung

Reaktionsgleichung von HRID 559821
[CH2:1]([NH:4][C:5]([C:7]1[C:8](=[O:24])[N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[C:10]([CH3:13])=[CH:11][CH:12]=1)=[O:6])[C:2]#[CH:3].[OH:25][N:26]=[C:27](Cl)[CH3:28].O>CCOC(C)=O>[CH3:28][C:27]1[CH:3]=[C:2]([CH2:1][NH:4][C:5]([C:7]2[C:8](=[O:24])[N:9]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=3)[C:10]([CH3:13])=[CH:11][CH:12]=2)=[O:6])[O:25][N:26]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 69633Ethanimidoyl chloride, N-hydroxy-HCID 866147846-Methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid prop-2-ynylamide

Produkt 1

HCID 667254586-Methyl-2-oxo-1-(3-trifluoromethylphenyl)-1,2-dihydro-pyridine-3-carboxylic acid (3-methyl-isoxazol-5-ylmethyl)-amideAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The compound obtained in step (a) (0.050 g, 0.15 mmol) was dissolved in EtOAc (15 ml) under magnetic stirring. To this solution was added N-hydroxyacetimidoyl chloride (0.15 g, 1.6 mmol), water (0.3 ml) and KHCO3 (0.16 g, 1.6 mmol). The mixture was stirred for 2 days at which time LC-MS showed 90% conversion. The reaction was stopped and the mixture was partitioned between EtOAc (25 ml) and water (25 ml). The organic phase was washed (water, brine) and dried. Filtration and evaporation gave a crude mixture which was purified by chromatography on silica. Freeze-drying the pure fractions afforded the subtitle compound (0.031 g, 53%) as a white powder.

Aufarbeitung

  1. customthe mixture was partitioned between EtOAc (25 ml) and water (25 ml)
  2. washThe organic phase was washed (water, brine)
  3. customdried
  4. filtrationFiltration and evaporation
  5. customgave a crude mixture which
  6. customwas purified by chromatography on silica
  7. customFreeze-drying the pure fractions

Quellen und Nachweise

ORD-Eintrag
ord-58f5b44017ee4ec284af8213ea33e467
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063073B2

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