Pyridine → HCID 19788676, compound

HRID 1656762Notes

Reaction equation

HRID 1656762 reaction equation
[F:1][C:2]1[C:3]([O:21][S:22]([CH3:25])(=[O:24])=[O:23])=[C:4]2[C:9]3=[C:10]([C:12](=[O:19])[C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][N:8]3[N:7]([CH3:20])[CH2:6][CH2:5]2)[CH:11]=1.N1C=CC=CC=1.[C:32]1([CH3:42])[CH:37]=[CH:36]C(S(Cl)(=O)=O)=[CH:34][CH:33]=1>C(Cl)(Cl)Cl>[F:1][C:2]1[C:3]([O:21][S:22]([C:25]2[CH:36]=[CH:37][C:32]([CH3:42])=[CH:33][CH:34]=2)(=[O:24])=[O:23])=[C:4]2[C:9]3=[C:10]([C:12](=[O:19])[C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][N:8]3[N:7]([CH3:20])[CH2:6][CH2:5]2)[CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 19788685HCID 19788685, compound

Product 1

HCID 19788676HCID 19788676, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

304 mg of the compound (168) obtained in Example 45 was added to 2 ml of pyridine, and 260 mg of p-toluene-sulfonyl chloride was added to the solution. The solution was stirred for 2 hours at room temperature. 50 ml of chloroform was added to the solution, and the solution was washed with water and aqueous 5% citric acid solution. The organic layer was separated, and after drying over magnesium sulfate, the solvent was removed by distillation. To the residue, ethanol was added, and the solid matter was filtered off and washed with isopropyl ether to obtain 220 mg of the subject compound (169).

Workup

  1. additionwas added to the solution
  2. washthe solution was washed with water and aqueous 5% citric acid solution
  3. customThe organic layer was separated
  4. dry with materialafter drying over magnesium sulfate
  5. customthe solvent was removed by distillation
  6. additionTo the residue, ethanol was added
  7. filtrationthe solid matter was filtered off
  8. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-b53169515c3c41cbbeeeeb81be52bb88
Source dataset
uspto-grants-1993_10
Patent number
US05254685

Reaction notes

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