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

HRID 748264Notes

Reaction equation

HRID 748264 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[C:5]([CH3:18])[CH:4]=1)#[N:2].[Cl:19][C:20]1[CH:21]=[C:22]([SH:29])[C:23](=[CH:27][CH:28]=1)[C:24](O)=[O:25]>N1C=CC=CC=1>[Cl:19][C:20]1[CH:28]=[CH:27][C:23]2[C:24](=[O:25])[N:2]=[C:1]([C:3]3[N:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH:6]=[C:5]([CH3:18])[CH:4]=3)[S:29][C:22]=2[CH:21]=1

Participants

4

Reactant 2

HCID 204569744-Chloro-2-sulfanylbenzoic acidHCID 22939494tert-Butyl 3-(6-cyano-4-methyl-2-pyridyl)propanoate

Product 1

HCID 22939347tert-Butyl 3-[6-(7-chloro-4-oxo-4H-1,3-benzothiazin-2-yl)-4-methyl-2-pyridyl]propanoateYield 28.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

tert-Butyl 3-(6-cyano-4-methyl-2-pyridyl)propanoate (0.69 g, 2.8 mmol) and 4-chlorothiosalicylic acid (1.05 g, 5.7 mmol) were dissolved in pyridine (10 ml). The mixture was refluxed for 22 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with hexane-ethyl acetate (3:1, v/v) were collected, concentrated and recrystallized from hexane-ethyl acetate to give the titled compound (0.33 g, 28%) as white crystals.

Workup

  1. temperatureThe mixture was refluxed for 22 hrs
  2. customThe solvent was evaporated
  3. washThe fractions eluted with hexane-ethyl acetate (3:1
  4. customv/v) were collected
  5. concentrationconcentrated
  6. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-f59773a3db184f38918b7599a516b112
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

Loading…