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Pyridine → 5-[1-(4-Methanesulfonylaminobenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione

HRID 504046
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 504046
ClCCl.[NH2:4][C:5]1[CH:32]=[CH:31][C:8]([CH2:9][N:10]2[C:19]3[C:14](=[C:15]([CH2:22][CH:23]4[S:27][C:26](=[O:28])[NH:25][C:24]4=[O:29])[CH:16]=[CH:17][C:18]=3[O:20][CH3:21])[CH2:13][CH2:12][C:11]2=[O:30])=[CH:7][CH:6]=1.N1C=CC=CC=1.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>O>[CH3:39][S:40]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[C:19]3[C:14](=[C:15]([CH2:22][CH:23]4[S:27][C:26](=[O:28])[NH:25][C:24]4=[O:29])[CH:16]=[CH:17][C:18]=3[O:20][CH3:21])[CH2:13][CH2:12][C:11]2=[O:30])=[CH:31][CH:32]=1)(=[O:42])=[O:41]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 866139395-[1-(4-Aminobenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione

Produkt 1

HCID 580267035-[1-(4-Methanesulfonylaminobenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione
Ausbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a dichloromethane (20 ml) solution of 1.00 g (0.00243 mM) of 5-[1-(4-aminobenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione were successively added pyridine (2.0 ml) and 0.21 ml (0.0027 mM) of methanesulfonyl chloride under ice cooling with stirring. The mixture was stirred at the same temperature for 30 minutes, and water was added to stop the reaction. The resultant was washed (twice with water and once with saturated sodium chloride solution), dried (magnesium sulfate), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:ethyl acetate=1:10→1:1), giving 1.1 g (92% yield) of the target compound as a white amorphous solid.

Aufarbeitung

  1. stirringThe mixture was stirred at the same temperature for 30 minutes
  2. customthe reaction
  3. washThe resultant was washed (twice with water
  4. dry with materialonce with saturated sodium chloride solution), dried (magnesium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (dichloromethane:ethyl acetate=1:10→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-958dc464092e43bd9855be6726d4a534
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07777038B2

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