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4-{3E-[5-(2-amino-phenylethynyl)-2,4-dimethoxy-phenyl]acryloyl}-N-(3-imidazol-1-ylpropyl)benzenesulfonamide → N-(3-Imidazol-1-yl-propyl)-4-{3E-[5-(1H-indol-2-yl)-2,4-dimethoxy-phenyl]acryloyl}benzenesulfonamide

HRID 347371
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HRID 347371 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]#[C:9][C:10]1[C:11]([O:40][CH3:41])=[CH:12][C:13]([O:38][CH3:39])=[C:14](/[CH:16]=[CH:17]/[C:18]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([NH:29][CH2:30][CH2:31][CH2:32][N:33]3[CH:37]=[CH:36][N:35]=[CH:34]3)(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[O:19])[CH:15]=1>C(#N)C.[Pd](Cl)Cl>[N:33]1([CH2:32][CH2:31][CH2:30][NH:29][S:26]([C:23]2[CH:22]=[CH:21][C:20]([C:18](=[O:19])/[CH:17]=[CH:16]/[C:14]3[CH:15]=[C:10]([C:9]4[NH:1][C:2]5[C:3]([CH:8]=4)=[CH:4][CH:5]=[CH:6][CH:7]=5)[C:11]([O:40][CH3:41])=[CH:12][C:13]=3[O:38][CH3:39])=[CH:25][CH:24]=2)(=[O:28])=[O:27])[CH:37]=[CH:36][N:35]=[CH:34]1
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참가 물질

4

반응물 1

HCID 694879324-{3E-[5-(2-amino-phenylethynyl)-2,4-dimethoxy-phenyl]acryloyl}-N-(3-imidazol-1-ylpropyl)benzenesulfonamide

생성물 1

HCID 11467239N-(3-Imidazol-1-yl-propyl)-4-{3E-[5-(1H-indol-2-yl)-2,4-dimethoxy-phenyl]acryloyl}benzenesulfonamide수율 100%

시약·촉매·용매 2

HCID 24290Palladium Chloride촉매HCID 6342Acetonitrile용매

실험 절차

A suspension of 4-{3E-[5-(2-amino-phenylethynyl)-2,4-dimethoxyphenyl]acryloyl}-N-(3-imidazol-1-ylpropyl)benzenesulfonamide (Ex-50A, 210 mg, 0.37 mmol) in acetonitrile (130 mL) was purged with nitrogen gas for 10 minutes. Palladium(II) chloride (5.0 mg, 0.029 mmol) was added to the reaction vessel. The reaction mixture was refluxed for 16 hrs. The cooled reaction mixture was stirred with 3-mercaptopropyl functionalized silica gel (500 mg) for 5 minutes. The filtrate was collected via suction filtration and concentrated to an orange solid to give 210 mg (100%) of the title compound, mp 197–200° C. 1H-NMR (300 MHz, DMSO-d6) 11.19 (br s, 1H), 8.28 (m, 3H), 8.11 (m, 2H), 7.95 (m, 4H), 7.45 (m, 3H), 7.00 (m, 5H), 4.08 (s, 3H), 4.03 (s, 3H), 3.89 (m, 2H), 2.69 (br s, 2H), 1.78 (br s, 2H). HRMS (ESI) Calcd. for C31H30N4O5S: 571.2015 [(M+H)+]; Found: 571.2016.

후처리

  1. customwas purged with nitrogen gas for 10 minutes
  2. temperatureThe reaction mixture was refluxed for 16 hrs
  3. customThe cooled reaction mixture
  4. filtrationThe filtrate was collected via suction filtration
  5. concentrationconcentrated to an orange solid

출처 및 근거

ORD 기록
ord-a0572ba6cf0b4e219fd8e8fcc6bfd63e
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07173129B2

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