4-Toluenesulfonyl chloride → 2,6-dichloro-N-{1-cyano-2-[2-(2,6-dichlorophenyl)-6-quinolinyl]ethyl}benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(2-amino-1-{[2-(2,6-dichlorophenyl)-6-quinolinyl]methyl}-2-oxoethyl)-2,6-dichlorobenzamide 122 (1.09 g) in pyridine (9 ml) is added p-toluenesulfonyl chloride (583 mg) at RT. The solution is stirred at 80° C. After one night, 120 mg of p-toluenesulfonyl chloride are added again to the mixture at RT to drive the reaction to completion. The solution is heated at 80° C. for one additional day. The organic phases are evaporated, AcOEt and a small amount of CH2Cl2 are added. The organic phases are washed 3 times with water, one time with a solution of NaHCO3, dried over MgSO4 and evaporated to dryness. The residue so obtained was purified over silica gel using CH2Cl2/CH3OH (99.25/0.75) as eluent to give 2,6-dichloro-N-{1-cyano-2-[2-(2,6-dichlorophenyl)-6-quinolinyl]ethyl}benzamide 58.

Provenance & Evidence