2-(Methylthio)benzylamine → 8-Hydroxy-5-bromo-[1,6]naphthyridine-7-carboxylic acid 2-methylsulfanylbenzylamide

HRID 897290

Reaktionsgleichung

Reaktionsgleichung von HRID 897290
CO[C:3]([C:5]1[C:14]([OH:15])=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[N:12]2)=[C:7]([Br:16])[N:6]=1)=[O:4].[CH3:17][S:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][NH2:22]>>[CH3:17][S:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][NH:22][C:3]([C:5]1[C:14]([OH:15])=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[N:12]2)=[C:7]([Br:16])[N:6]=1)=[O:4]

Komponenten

3

Edukt 2

HCID 27369812-(Methylthio)benzylamineHCID 22343006Methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylate

Produkt 1

HCID 865874628-Hydroxy-5-bromo-[1,6]naphthyridine-7-carboxylic acid 2-methylsulfanylbenzylamide

Versuchsvorschrift

To a 25 mL round bottomed flask with a stirring bar, reflux condenser and a nitrogen inlet was added 5-bromo-8-hydroxy-[1,6]naphthyridine-7-carboxylic acid methyl ester (0.511 g, 1.81 mmol) dry toluene (12.5 mL) and 2-methylthiobenzylamine (0.346 g, 2.26 mmol). This mixture was heated at reflux for 24 h. The mixture was cooled to ambient temperature and the toluene was removed in vacuo. The residue was triturated with a little Et2O/hexane, collected on a frit and dried in vacuo to give 8-hydroxy-5-bromo-[1,6]naphthyridine-7-carboxylic acid 2-methylsulfanylbenzylamide as a crystalline solid.

Aufarbeitung

  1. temperatureTo a 25 mL round bottomed flask with a stirring bar, reflux condenser and a nitrogen inlet
  2. temperatureThis mixture was heated
  3. temperatureat reflux for 24 h
  4. customthe toluene was removed in vacuo
  5. customThe residue was triturated with a little Et2O/hexane
  6. customcollected on a frit
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a8c37aa63e1d4c4cbe671ee3dd767aa9
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921759B2

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