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

HRID 897290

Reaction equation

HRID 897290 reaction equation
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]

Participants

3

Reactant 2

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a8c37aa63e1d4c4cbe671ee3dd767aa9
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Linked notes

Loading…