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

HRID 1869806Notes

Reaction equation

HRID 1869806 reaction equation
[NH2:1][C:2](=O)[CH:3]([NH:23][C:24](=[O:33])[C:25]1[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:32])[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:22])[CH:9]=[CH:8]2.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>N1C=CC=CC=1>[Cl:32][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]([Cl:31])[C:25]=1[C:24]([NH:23][CH:3]([C:2]#[N:1])[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:22])[CH:9]=[CH:8]2)=[O:33]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chloride2×HCID 57987641N-(2-amino-1-{[2-(2,6-dichlorophenyl)-6-quinolinyl]methyl}-2-oxoethyl)-2,6-dichlorobenzamide

Product 1

HCID 685928212,6-dichloro-N-{1-cyano-2-[2-(2,6-dichlorophenyl)-6-quinolinyl]ethyl}benzamideYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  1. waitAfter one night
  2. customthe reaction to completion
  3. temperatureThe solution is heated at 80° C. for one additional day
  4. customThe organic phases are evaporated
  5. additionAcOEt and a small amount of CH2Cl2 are added
  6. washThe organic phases are washed 3 times with water, one time with a solution of NaHCO3
  7. dry with materialdried over MgSO4
  8. customevaporated to dryness
  9. customThe residue so obtained
  10. customwas purified over silica gel

Sources & evidence

ORD record
ord-3189de1352c94f0d8aac5d51983e3c7e
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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