Dimethylamine → 2-{2-[4-(1-Dimethylamino-ethyl)-2-methyl-phenyl]-2-oxo-ethyl}-5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one

HRID 1425773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1425773
Br[CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:29])[CH2:11][N:12]2[C:17](=[O:18])[CH:16]=[C:15]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][N:22]=3)[CH:14]=[N:13]2)=[C:6]([CH3:30])[CH:5]=1)[CH3:3].[CH3:31][NH:32][CH3:33]>C(Cl)Cl>[CH3:31][N:32]([CH3:33])[CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:29])[CH2:11][N:12]2[C:17](=[O:18])[CH:16]=[C:15]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][N:22]=3)[CH:14]=[N:13]2)=[C:6]([CH3:30])[CH:5]=1)[CH3:3]

Komponenten

4

Edukt 2

HCID 674DimethylamineHCID 866955602-{2-[4-(1-Bromo-ethyl)-2-methyl-phenyl]-2-oxo-ethyl}-5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one

Produkt 1

HCID 717309172-{2-[4-(1-Dimethylamino-ethyl)-2-methyl-phenyl]-2-oxo-ethyl}-5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-{2-[4-(1-Bromo-ethyl)-2-methyl-phenyl]-2-oxo-ethyl}-5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one (preparation 10d, 1.55 g, 3.28 mmol) in CH2Cl2 (5 mL) is added a solution of dimethylamine (2 M in THF, 4.9 mL, 9.8 mmol). The reaction mixture is stirred overnight at room temperature. After dilution with CH2Cl2, the mixture is washed with aqueous NaHCO3 solution. The organic layer is dried over MgSO4 and evaporated under reduced pressure. The crude product is purified via reverse phase HPLC chromatography (Phenomenex Gemini C18, gradient 30%→95% methanol in water+0.1% NH4OH, 120 mL/min).

Aufarbeitung

  1. washAfter dilution with CH2Cl2, the mixture is washed with aqueous NaHCO3 solution
  2. dry with materialThe organic layer is dried over MgSO4
  3. customevaporated under reduced pressure
  4. customThe crude product is purified via reverse phase HPLC chromatography (Phenomenex Gemini C18, gradient 30%→95% methanol in water+0.1% NH4OH, 120 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-d509285c26d740368ce2bfda5b76cc2d
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933079B2

Notizen zur Reaktion

Wird geladen…