Triethylamine → HCID 12988026, Verbindung

HRID 1582979Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1582979
Cl.[CH2:2]([N:4]=[C:5]=NCCCN(C)C)C.Cl.CNC.C(N(CC)CC)C.[Cl:24][C:25]1[CH:26]=[C:27]([C:31]2[C:40]3[C:35](=[N:36][C:37]([CH3:41])=[CH:38][CH:39]=3)[N:34]([CH2:42][CH3:43])[C:33](=[O:44])[C:32]=2[CH2:45][CH2:46][C:47]([OH:49])=O)[CH:28]=[CH:29][CH:30]=1>O.CN(C=O)C>[Cl:24][C:25]1[CH:26]=[C:27]([C:31]2[C:40]3[C:35](=[N:36][C:37]([CH3:41])=[CH:38][CH:39]=3)[N:34]([CH2:42][CH3:43])[C:33](=[O:44])[C:32]=2[CH2:45][CH2:46][C:47]([N:4]([CH3:5])[CH3:2])=[O:49])[CH:28]=[CH:29][CH:30]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10156040337357-62-7

Produkt 1

HCID 12988026HCID 12988026, VerbindungAusbeute 34,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Under ice cooling, 630 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 154 mg of dimethylamine hydrochloride and 0.53 ml of triethylamine were added successively to a 10 ml DMF solution containing 700 mg of 3-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acid. The reaction mixture was warmed to room temperature and stirred for 2 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and then the solvent was evaporated. The residue was purified by a silica gel column chromatography (chloroform-ethyl acetate) and then recrystallized from diisopropyl ether to obtain 262 mg of 3-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]-N,N-dimethylpropanamide as colorless crystals.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customthe solvent was evaporated
  4. customThe residue was purified by a silica gel column chromatography (chloroform-ethyl acetate)
  5. customrecrystallized from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-2011cd4e13064cdcb2a60359b4381e4a
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06740662B1

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