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

HRID 331202노트

반응식

HRID 331202 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

N-(3,5-dimethoxyphenyl)quinoxaline-2,3-diamine (50 mg, 0.168 mmol), 3-Acetylamino benzene 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.

후처리

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

출처 및 근거

ORD 기록
ord-de33e6f9212842ceb0c0fc0749291dea
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877757B2

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