Pyridine → HCID 19788676, compound

HRID 1609086Notes

Reaction equation

HRID 1609086 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])[CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:14][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 20083137HCID 20083137, compound

Product 1

HCID 19788676HCID 19788676, compound

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 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-a38f361d6dec48e8b3d9e5bd54289f3d
Source dataset
uspto-grants-1995_03
Patent number
US05399553

Reaction notes

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