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

HRID 499259Notes

Reaction equation

HRID 499259 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-3566cc727aa54599965bbcd6adc14fe9
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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