Triethylamine → 4-Chloro-N-[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-butyramide

HRID 548828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 548828
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[N:20]=[N:19][C:18]([NH2:21])=[CH:17][CH:16]=1.C(N(CC)CC)C.[Cl:29][CH2:30][CH2:31][CH2:32][C:33](Cl)=[O:34]>C1COCC1>[Cl:29][CH2:30][CH2:31][CH2:32][C:33]([NH:21][C:18]1[N:19]=[N:20][C:15]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:5][O:6][C:2]=2[CH3:1])=[CH:16][CH:17]=1)=[O:34]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 426297716-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-ylamine

Produkt 1

HCID 671580934-Chloro-N-[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-butyramideAusbeute 54,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-ylamine (1.0 g, 3.5 mmol) in THF (15 ml) was added triethylamine (0.59 mL, 4.3 mmol). The mixture was cooled in an ice bath and a solution of 4-chlorobutyryl chloride (0.48 mL, 4.3 mmol) in THF (5 mL) was added dropwise. After stirring for 1 h at room temperature the precipitate was filtered and the organic phase was evaporated. The residue was dissolved in methanol (20 mL), sodium bicarbonate (1 spatula) was added and the mixture was stirred at room temperature for 1 h. The solvent was evaporated and the residue was extracted (dichloromethane/water). Then the organic phase was dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, heptane/ethyl acetate=100:0 to 60:40) afforded the title compound (740 mg, 54%) (as the least polar component of two formed in the reaction) which was obtained as a white solid. MS: m/e=387.3 [M+H]+.

Aufarbeitung

  1. temperatureThe mixture was cooled in an ice bath
  2. filtrationwas filtered
  3. customthe organic phase was evaporated
  4. dissolutionThe residue was dissolved in methanol (20 mL)
  5. additionsodium bicarbonate (1 spatula) was added
  6. stirringthe mixture was stirred at room temperature for 1 h
  7. customThe solvent was evaporated
  8. extractionthe residue was extracted (dichloromethane/water)
  9. dry with materialThen the organic phase was dried over sodium sulfate
  10. concentrationconcentrated
  11. customPurification by chromatography (SiO2, heptane/ethyl acetate=100:0 to 60:40)

Quellen und Nachweise

ORD-Eintrag
ord-21e4f2d6cb1f418781cc83e1e3c888fa
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943619B2

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