Water → HCID 44608544, Verbindung

HRID 1943687

Reaktionsgleichung

Reaktionsgleichung von HRID 1943687
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:7]=[N:8][CH:9]=[CH:10][C:2]1=2.[CH3:11][O:12][C:13]1[CH:17]=[C:16]([C:18](Cl)=[O:19])[O:15][N:14]=1.C(N(CC)CC)C.O>ClCCl>[O:1]1[CH2:6][CH2:5][N:4]([C:18]([C:16]2[O:15][N:14]=[C:13]([O:12][CH3:11])[CH:17]=2)=[O:19])[C:3]2[CH:7]=[N:8][CH:9]=[CH:10][C:2]1=2

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 121963593-Methoxy-5-isoxazolecarbonyl chlorideHCID 218859502H,3H,4H-pyrido[4,3-b][1,4]oxazine

Produkt 1

HCID 44608544HCID 44608544, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a 10 ml flask, 3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (100 mg, 0.73 mmol) and 3-methoxy-isoxazol-5-carbonyl chloride (131 mg, 0.80 mmol) were dissolved in dichloromethane. Triethylamine (0.51 ml, 3.65 mmol) was added thereto and then stirred at room temperature for 2 hours. After completion of the reaction by adding water dropwise, the reaction mixture was extracted with dichloromethane, and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on amine silica eluting with a solvent of dichloromethane:methanol=30:1. The fractions containing the product were collected and evaporated to obtain the target compound 43, i.e., (2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-(3-methoxy-isoxazol-5-yl)-methanone, as pale-brown solid (149 mg, 78%).

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionthe reaction mixture was extracted with dichloromethane
  3. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on amine silica eluting with a solvent of dichloromethane
  7. additionThe fractions containing the product
  8. customwere collected
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-bf094ab021954322a9bee2d356e54902
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394792B2

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