4-Bromoaniline → N-(4-Bromo-phenyl)-2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-(2,2-difluoro-ethoxy)-1H-benzimidazole-5-carboxylic acid amide

HRID 410095노트

반응식

HRID 410095 반응식
[Cl:1][C:2]1[C:7]([CH2:8][NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=[C:4]([Cl:16])[C:3]=1[NH:17][C:18]1[NH:22][C:21]2[CH:23]=[C:24]([O:30][CH2:31][CH:32]([F:34])[F:33])[C:25]([C:27]([OH:29])=O)=[CH:26][C:20]=2[N:19]=1.[Br:35][C:36]1[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=1.C1COCC1>CCOC(C)=O>[Br:35][C:36]1[CH:42]=[CH:41][C:39]([NH:40][C:27]([C:25]2[C:24]([O:30][CH2:31][CH:32]([F:33])[F:34])=[CH:23][C:21]3[NH:22][C:18]([NH:17][C:3]4[C:4]([Cl:16])=[CH:5][CH:6]=[C:7]([CH2:8][NH:9][C:10](=[O:15])[C:11]([CH3:13])([CH3:12])[CH3:14])[C:2]=4[Cl:1])=[N:19][C:20]=3[CH:26]=2)=[O:29])=[CH:38][CH:37]=1

참가 물질

5

반응물 3

HCID 78074-BromoanilineHCID 8028TetrahydrofuranHCID 1784473262-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-(2,2-difluoro-ethoxy)-1H-benzimidazole-5-carboxylic acid

생성물 1

HCID 178447321N-(4-Bromo-phenyl)-2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-(2,2-difluoro-ethoxy)-1H-benzimidazole-5-carboxylic acid amide

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

PPA (0.223 mL, 50% in EtOAc, ˜0.38 mmol) is slowly added to a mixture of 2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-(2,2-difluoro-ethoxy)-1H-benzimidazole-5-carboxylic acid (0.150 g, 0.291 mmol), 4-bromoaniline (50 mg, 0.291 mmol), TEA (0.101 mL, 0.728 mmol) and THF (10 mL). The mixture is refluxed for 3 d, concentrated and purified via prep. HPLC (column: Zorbax stable bond C18, 5 μm, 30×100 mm, gradient: water+0.15% HCOOH/MeOH 95:5→10:90) to furnish the title compound.

후처리

  1. temperatureThe mixture is refluxed for 3 d
  2. concentrationconcentrated
  3. custompurified via prep

출처 및 근거

ORD 기록
ord-b71aef7baeae4d69bb02ca0bb9b2ddba
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759537B2

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