Thiophenol → HCID 10115217, compound

HRID 897282Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([Cl:24])[CH:23]=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>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([Cl:24])[CH:23]=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

Reactant 3

HCID 7969Thiophenol

HCID 8471Triethylamine

HCID 10180885HCID 10180885, compound

Product 1

HCID 10115217HCID 10115217, compound

Conditions

Temperature: 135 °C

Procedure

To a 5 mL pyrex pressure vessel with a stirring bar was added 5-bromo-8-hydroxy-[1,6]naphthyridine-7-carboxylic acid 3,5-dichloro-benzylamide (0.055 g, 0.13 mmol), thiophenol (0.056 g, 0.50 mmol) and triethylamine (0.28 mL, 2.00 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 on silica gel (15 g) using methanol:chloroform (5:95) as eluant to give 8-hydroxy-5-phenylsulfanyl-[1,6]naphthyridine-7-carboxylic acid 3,5-dichlorobenzylamide as a solid.

Workup

customThe vessel was sealed under nitrogen
customThe cooled reaction mixture
concentrationwas concentrated in vacuo
customthe residue was chromatographed on silica gel (15 g)

Sources & evidence

ORD record: ord-4c1fa22ee4954908aec46973d8105727
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921759B2

Reaction notes

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