Triethylamine → tert-Butyl (6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methylcarbamate

HRID 499467Notes

Reaction equation

HRID 499467 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:6]=[CH:5][CH:4]=1)#[N:2].[C:18](OC)(=[O:26])[C:19]1[C:20](=[CH:22][CH:23]=[CH:24][CH:25]=1)[SH:21].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:26]=[C:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[S:21][C:1]([C:3]2[N:8]=[C:7]([CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH:6]=[CH:5][CH:4]=2)=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939432tert-Butyl 6-cyano-2-pyridylmethylcarbamate

Product 1

HCID 59750386tert-Butyl (6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methylcarbamateYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl (6-cyano-2-pyridyl)methylcarbamate (1.6 g, 6.8 mmol) and methyl thiosalicylate (1.8 g, 10.9 mmol) were dissolved in toluene (6 ml), and triethylamine (3.0 ml, 21.5 mmol) was added thereto. The mixture was refluxed for 20 hrs. After cooling, the precipitates were collected by filtration and dissolved in chloroform. The solution was subjected to a silica gel column chromatography. The fractions eluted with chloroform-methanol (20:1, v/v) were collected, concentrated and recrystallized from hexane-chloroform to give the titled compound (1.8 g, 72%) as pale yellow crystals.

Workup

  1. temperatureThe mixture was refluxed for 20 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitates were collected by filtration
  4. dissolutiondissolved in chloroform
  5. washThe fractions eluted with chloroform-methanol (20:1
  6. customv/v) were collected
  7. concentrationconcentrated
  8. customrecrystallized from hexane-chloroform

Sources & evidence

ORD record
ord-199fe2f7b6134c3db314c233bfdbb1fe
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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