2-Pyridinemethanamine → 5-methyl-3-phenyl-N-(pyridin-2-ylmethyl)-1,2-oxazole-4-carboxamide

HRID 747857

Reaktionsgleichung

Reaktionsgleichung von HRID 747857
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH2:8].C(=O)([O-])O.[Na+].[CH3:14][C:15]1[O:19][N:18]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:16]=1[C:26](Cl)=[O:27]>O.C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:26]([C:16]1[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:18][O:19][C:15]=1[CH3:14])=[O:27]

Komponenten

6

Edukt 3

HCID 195092-PyridinemethanamineHCID 856245-Methyl-3-phenylisoxazole-4-carbonyl chlorideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 7008625-methyl-3-phenyl-N-(pyridin-2-ylmethyl)-1,2-oxazole-4-carboxamideAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel3×

Versuchsvorschrift

A mixture of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid (4.06 g, 20 mmol, commercially available) and thionyl chloride (5 mL) was heated under reflux for 3 h. Evaporation of all volatiles afforded 5-methyl-3-phenyl-isoxazole-4-carboxylic acid chloride (4.4 g, 93%) as yellow oil, which was used without further purification in the next reaction. To a mixture of an aqueous solution of 2-picolylamine (0.182 g, 1.68 mmol) in water (2 mL) and ethyl acetate (4 mL) were added sodium hydrogen carbonate (362 mg, 4.2 mmol) in one portion. Then, 5-methyl-3-phenyl-isoxazole-4-carboxylic acid chloride (0.31 g, 1.4 mmol) in ethyl acetate (2 mL) was added dropwise with vigorous stirring under ice-bath cooling keeping the temperature at 0° C. After addition, the reaction mixture was stirred at room temperature for 18 h. The resulting solution was then diluted with ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined extracts were then washed with brine, dried over sodium sulphate) and concentrated to afford the title compound (0.38 g, 93%) as a white solid. MS: m/e: 294.1 [M+H]+.

Aufarbeitung

  1. customwas used without further purification in the next reaction
  2. temperaturecooling
  3. customat 0° C
  4. additionAfter addition
  5. stirringthe reaction mixture was stirred at room temperature for 18 h
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washThe combined extracts were then washed with brine
  9. dry with materialdried over sodium sulphate) and
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6a68f2577e1647dd9cb47a104f332755
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399769B2

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