1,4-Dichlorobenzene → N-{3-[({3-[(3,5-dimethoxyphenyl)amino]quinoxalin-2-yl}amino)sulfonyl]phenyl}acetamide

HRID 655629Notes

Reaction equation

HRID 655629 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:21]([NH2:22])=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[C:23]([NH:26][C:27]1[CH:28]=[C:29]([S:33](Cl)(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1)(=[O:25])[CH3:24].C1C(Cl)=CC=C(Cl)C=1>N1C=CC=CC=1>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([NH:11][C:12]2[C:21]([NH:22][S:33]([C:29]3[CH:28]=[C:27]([NH:26][C:23](=[O:25])[CH3:24])[CH:32]=[CH:31][CH:30]=3)(=[O:35])=[O:34])=[N:20][C:19]3[C:14]([N:13]=2)=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 3

HCID 46851,4-DichlorobenzeneHCID 31574553-Acetamidobenzene-1-sulfonyl chlorideHCID 16045834N-(3,5-dimethoxyphenyl)quinoxaline-2,3-diamine

Product 1

HCID 16045462N-{3-[({3-[(3,5-dimethoxyphenyl)amino]quinoxalin-2-yl}amino)sulfonyl]phenyl}acetamideYield 24%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-(3,5-dimethoxyphenyl)quinoxaline-2,3-diamine (50 mg, 0.168 mmol), 3-Acetylaminobenzene sulfonylchloride (59 mg, 0.5 mmol, commercially available from INTERCHIM) are dissolved in a 1 to 2 mixture of pyridine: dichlorobenzene (0.3 ml) and the reaction mixture is heated to 150° C. overnight in an orbital shaker. When TLC confirms the total consumption of the starting material, the reaction mixture is cooled down to rt. The precipitate formed is filtered and purified by column chromatography, using Pet.Ether: EtOAc as eluent, to afford 20 mg (24%) of the title compound as a yellow solid. HPLC (max plot) 89%, rt. 4.08 min. LC/MS: (ES+): 494.

Workup

  1. customthe total consumption of the starting material
  2. customThe precipitate formed
  3. filtrationis filtered
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-7643e269768a423fa2a28779aecf8184
Source dataset
uspto-grants-2011_12
Patent number
US08071597B2

Reaction notes

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