Pyridine → HCID 22675419, compound

HRID 1005958Notes

Reaction equation

HRID 1005958 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[N:12]([C:13]([CH3:15])=[CH2:14])[C:11]2[CH:16]=[CH:17][CH:18]=[CH:19][C:10]=2[N:9]=1.N1C=CC=CC=1.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>ClCCl>[S:32]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[N:12]([C:13]([CH3:15])=[CH2:14])[C:11]2[CH:16]=[CH:17][CH:18]=[CH:19][C:10]=2[N:9]=1)([C:29]1[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=1)(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 22643415HCID 22643415, compound

Product 1

HCID 22675419HCID 22675419, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2 g of the compound obtained in Example 14a in 20 ml of dichloromethane was added with 5 ml of pyridine and 1.8 g of p-toluenesulfonyl chloride and stirred for 5 hours. The organic layer was washed with 10% aqueous citric acid and then with water, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane) to obtain 2.2 g of the title compound (yield: 69%).

Workup

  1. washThe organic layer was washed with 10% aqueous citric acid
  2. dry with materialwith water, and dried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-c17fcd7118544b74bfa4e8c9879a7b6c
Source dataset
uspto-grants-2004_09
Patent number
US06787561B1

Reaction notes

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