Water → {2-[5-(4-Benzyloxy-phenyl)-6-butyl-pyridazin-3-yloxy]-ethyl}-diethyl-amine

HRID 401870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 401870
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][OH:6])[CH3:2].[H-].[Na+].[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[C:29](Cl)[N:28]=[N:27][C:26]=2[CH2:32][CH2:33][CH2:34][CH3:35])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>C1COCC1>[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[C:29]([O:6][CH2:5][CH2:4][N:3]([CH2:7][CH3:8])[CH2:1][CH3:2])[N:28]=[N:27][C:26]=2[CH2:32][CH2:33][CH2:34][CH3:35])=[CH:21][CH:20]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7497DiethylethanolamineHCID 24758Sodium hydrideHCID 713030894-(4-(Benzyloxy)phenyl)-3-butyl-6-chloropyridazine

Produkt 1

HCID 53371810{2-[5-(4-Benzyloxy-phenyl)-6-butyl-pyridazin-3-yloxy]-ethyl}-diethyl-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-diethylamino-ethanol (0.42 mmol, 50 mg) in THF at room temperature was added NaH (0.85 mmol, 20 mg). Stirring continued for 10 min then 4-(4-benzyloxy-phenyl)-3-butyl-6-chloro-pyridazine (Example 1, 0.14 mmol, 50 mg) was added. The resulting mixture was stirred at 50-55° C. overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The product was purified by column chromatography using 10% methanolic solution of ammonia (2.0 M ammonia in methanol) in ethyl acetate to provide {2-[5-(4-benzyloxy-phenyl)-6-butyl-pyridazin-3-yloxy]-ethyl}-diethyl-amine.

Aufarbeitung

  1. stirringThe resulting mixture was stirred at 50-55° C. overnight
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c8a4c47f4ca243fc83c3ecb6f9d766a1
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741900B2

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