2-Mercapto-4-(trifluoromethyl)benzoic acid → tert-Butyl 3-[6-(4-oxo-7-trifluoromethyl-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoate

HRID 499424Notes

Reaction equation

HRID 499424 reaction equation
[SH:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:15]([C:17]1[N:22]=[C:21]([CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:20]=[CH:19][CH:18]=1)#[N:16]>N1C=CC=CC=1>[O:6]=[C:4]1[C:3]2[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:10][C:2]=2[S:1][C:15]([C:17]2[N:22]=[C:21]([CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:20]=[CH:19][CH:18]=2)=[N:16]1

Participants

4

Reactant 2

HCID 215421322-Mercapto-4-(trifluoromethyl)benzoic acidHCID 22939301Tert-butyl 3-(6-cyano-2-pyridyl)propanoate

Product 1

HCID 22939516tert-Butyl 3-[6-(4-oxo-7-trifluoromethyl-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoateYield 34.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Mercapto-4-trifluoromethylbenzoic acid (1.59 g, 7.2 mmol) and tert-butyl 3-(6-cyano-2-pyridyl)propanoate (1.32 g, 5.7 mmol) were dissolved in pyridine (15 ml), and the mixture was refluxed for 15 hrs. The reaction mixture was concentrated under reduced pressure, subjected to a silica gel column chromatography, eluted with hexane-ethyl acetate (3:1, v/v) and recrystallized from ethyl acetate-hexane to give the titled compound (0.85 g, 34%).

Workup

  1. temperaturethe mixture was refluxed for 15 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washeluted with hexane-ethyl acetate (3:1
  4. customv/v) and recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8dc86e302e824c8991629694b903145a
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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