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

HRID 499421Notes

Reaction equation

HRID 499421 reaction equation
[SH:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:13]([C:15]1[N:20]=[C:19]([CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:18]=[CH:17][CH:16]=1)#[N:14]>N1C=CC=CC=1>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:3]2[C:4](=[O:6])[N:14]=[C:13]([C:15]3[N:20]=[C:19]([CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:18]=[CH:17][CH:16]=3)[S:1][C:2]=2[CH:10]=1

Participants

4

Reactant 2

HCID 139616424-Methoxy-2-sulfanylbenzoic acidHCID 22939301Tert-butyl 3-(6-cyano-2-pyridyl)propanoate

Product 1

HCID 22939580tert-Butyl 3-[6-(7-methoxy-4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoateYield 46.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Mercapto-4-methoxybenzoic acid (1.26 g, 6.8 mmol) and tert-butyl 3-(6-cyano-2-pyridyl)propanoate (1.21 g, 5.2 mmol) were dissolved in pyridine (10 ml), and the reaction mixture was refluxed for 24 hrs. The reaction mixture was concentrated under reduced pressure, subjected to a silica gel column chromatography, eluted with hexane-ethyl acetate (1:1, v/v) and recrystallized from ethyl acetate-hexane to give the titled compound (0.96 g, 46%).

Workup

  1. temperaturethe reaction mixture was refluxed for 24 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washeluted with hexane-ethyl acetate (1:1
  4. customv/v) and recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-86674784bc954a69af97fe5a8f3c0a76
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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