Potassium Carbonate → (S)-ethyl 6-bromo-1-(1-(2-morpholinoethyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1047159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047159
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[N:11][CH:12]=1)[N:9]([C@H:13]1[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]1)[CH:8]=[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:6]2=[O:24].C([O-])([O-])=O.[K+].[K+].Cl.Br[CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>C(#N)C>[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[N:11][CH:12]=1)[N:9]([C@H:13]1[CH2:18][CH2:17][CH2:16][N:15]([CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[CH2:14]1)[CH:8]=[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:6]2=[O:24]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 129555404-(2-Bromoethyl)morpholine hydrochlorideHCID 86665046(S)-ethyl 6-bromo-4-oxo-1-(piperidin-3-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate hydrochloride

Produkt 1

HCID 69621275(S)-ethyl 6-bromo-1-(1-(2-morpholinoethyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

(S)-ethyl 6-bromo-4-oxo-1-(piperidin-3-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate hydrochloride Intermediate 33, 0.400 g, 0.96 mmol) and K2CO3 (0.663 g, 4.80 mmol) were taken up in acetonitrile (3 mL) and 4-(2-bromoethyl)morpholine hydrochloride (0.221 g, 0.96 mmol) added. The reaction mixture was heated to 120° C. in the microwave for 30 min. The reaction mixture was cooled to room temperature and filtered, and the inorganics were washed with EtOAc two times. The solvent was removed in vacuo. (S)-ethyl 6-bromo-1-(1-(2-morpholinoethyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (0.420 g, 89%) was recovered as a tan solid and will be carried on without further purification. MS (ES)(M+H)+: 494 for C22H29BrN4O4.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washthe inorganics were washed with EtOAc two times
  4. customThe solvent was removed in vacuo
  5. custom(S)-ethyl 6-bromo-1-(1-(2-morpholinoethyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (0.420 g, 89%) was recovered as a tan solid
  6. customwill be carried on without further purification

Quellen und Nachweise

ORD-Eintrag
ord-a05205c87013454993e89832e700d999
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569484B2

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