4-Chloro-2-sulfanylbenzoic acid → tert-Butyl 3-[6-(7-chloro-4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoate

HRID 748081Notes

Reaction equation

HRID 748081 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([SH:11])[CH:3]=1.[C:12]([C:14]1[N:19]=[C:18]([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:17]=[CH:16][CH:15]=1)#[N:13]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2[C:6](=[O:8])[N:13]=[C:12]([C:14]3[N:19]=[C:18]([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:17]=[CH:16][CH:15]=3)[S:11][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 204569744-Chloro-2-sulfanylbenzoic acidHCID 22939301Tert-butyl 3-(6-cyano-2-pyridyl)propanoate

Product 1

HCID 22939302tert-Butyl 3-[6-(7-chloro-4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoateYield 51.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Chloro-2-mercaptobenzoic acid (2.60 g, 13.7 mmol) and tert-butyl 3-(6-cyano-2-pyridyl)propanoate (1.60 g, 6.9 mmol) were dissolved in pyridine (15 ml), and the mixture was refluxed for 13 hrs. The reaction mixture was concentrated under reduced pressure, subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (3:1, v/v) to give the titled compound (1.42 g, 51%).

Workup

  1. temperaturethe mixture was refluxed for 13 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washeluted with hexane-ethyl acetate (3:1

Sources & evidence

ORD record
ord-6abe862eec5a404f9787a66576da2cb6
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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