Thiophenol → 8-Hydroxy-5-phenylsulfanyl-[1,6]naphthyridine-7-carboxylic acid 2-methylsulfanylbenzylamide

HRID 897291Notes

Reaction equation

HRID 897291 reaction equation
[CH3:1][S:2][C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[CH2:5][NH:6][C:7]([C:9]1[C:18]([OH:19])=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[C:11](Br)[N:10]=1)=[O:8].[C:25]1([SH:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>>[CH3:1][S:2][C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[CH2:5][NH:6][C:7]([C:9]1[C:18]([OH:19])=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[C:11]([S:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:10]=1)=[O:8]

Participants

4

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 865874628-Hydroxy-5-bromo-[1,6]naphthyridine-7-carboxylic acid 2-methylsulfanylbenzylamide

Product 1

HCID 208168678-Hydroxy-5-phenylsulfanyl-[1,6]naphthyridine-7-carboxylic acid 2-methylsulfanylbenzylamide

Conditions

Temperature
135 °C

Procedure

To a 5 mL pyrex pressure vessel with a stirring bar was added 8-hydroxy-5-bromo-[1,6]naphthyridine-7-carboxylic acid 2-methylsulfanylbenzylamide (0.22 g, 0.54 mmol), thiophenol (0.181 g, 1.63 mmol) and triethylamine (0.557 mL, 4.00 mmol). The vessel was sealed under nitrogen and the stirred mixture heated in a 135° C. oil bath for 24 h. The cooled reaction mixture was concentrated in vacuo and the residue was chromatographed by reverse phase HPLC using water/acetonitrile as eluant to give 8-hydroxy-5-phenylsulfanyl-[1,6]naphthyridine-7-carboxylic acid 2-methylsulfanylbenzylamide as a solid.

Workup

  1. customThe vessel was sealed under nitrogen
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated in vacuo
  4. customthe residue was chromatographed by reverse phase

Sources & evidence

ORD record
ord-39f68ebea5bc43a9aaa9f557cd9ab7ca
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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