N,N-Dimethylethylenediamine → Ethyl 6-bromo-1-[2-(dimethylamino)ethyl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1047149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047149
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([CH2:12][CH2:13]OS(C)(=O)=O)[CH:7]=[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:5]2=[O:24].[CH3:25][N:26](C)[CH2:27]CN>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([CH2:12][CH2:13][N:26]([CH3:27])[CH3:25])[CH:7]=[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:5]2=[O:24]

Komponenten

4

Edukt 2

HCID 66053N,N-DimethylethylenediamineHCID 86665044Ethyl 6-bromo-1-{2-[(methylsulfonyl)oxy]ethyl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate2×

Produkt 1

HCID 68747522Ethyl 6-bromo-1-[2-(dimethylamino)ethyl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylateAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of ethyl 6-bromo-1-{2-[(methylsulfonyl)oxy]ethyl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (Intermediate 20, 700 mg, 1.67 mmol) in dichloromethane was purged with N,N-dimethylethane-1,2-diamine gas until the starting material disappeared. The reaction mixture was washed with water, and the organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford ethyl 6-bromo-1-[2-(dimethylamino)ethyl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate 300 mg, (49%).

Aufarbeitung

  1. washThe reaction mixture was washed with water
  2. dry with materialthe organic layer was dried over anhydrous sodium sulphate
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1f30386bd19d408aafe454934dfd995b
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569484B2

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