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1,2-Dimethoxyethane → 1-Isopropylsulfonyl-2-amino-6-(1-(benzyl)-5-(3,5-difluorophenyl)-2-(2,4-difluorophenyl)-imidazol-4-yl)-benzimidazole

HRID 2252030
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HRID 2252030 반응식
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[CH:14]=2)=[C:11](Br)[N:10]=[C:9]1[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=1[F:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:30]([S:33]([N:36]1[C:40]2[CH:41]=[C:42](B(O)O)[CH:43]=[CH:44][C:39]=2[N:38]=[C:37]1[NH2:48])(=[O:35])=[O:34])([CH3:32])[CH3:31].C(=O)([O-])[O-].[Na+].[Na+].COCCOC>C(OCC)(=O)C>[CH:30]([S:33]([N:36]1[C:40]2[CH:41]=[C:42]([C:11]3[N:10]=[C:9]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=4[F:29])[N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:12]=3[C:13]3[CH:14]=[C:15]([F:20])[CH:16]=[C:17]([F:19])[CH:18]=3)[CH:43]=[CH:44][C:39]=2[N:38]=[C:37]1[NH2:48])(=[O:34])=[O:35])([CH3:32])[CH3:31]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 179816431-Benzyl-4-bromo-5-(3,5-difluoro-phenyl)-2-(2,4-difluoro-phenyl)-imidazoleHCID 17981723HCID 17981723, 화합물

생성물 1

HCID 179817671-Isopropylsulfonyl-2-amino-6-(1-(benzyl)-5-(3,5-difluorophenyl)-2-(2,4-difluorophenyl)-imidazol-4-yl)-benzimidazole수율 104.3%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Reflux a mixture of 1-benzyl-4-bromo-5-(3,5-difluoro-phenyl)-2-(2,4-difluoro-phenyl)-imidazole (0.061 g, 0.13 mmol), 1-isopropylsulfonyl-2-amino-benzimidazole-6-boronic acid (0.113 g, 0.40 mmol) (described in preparation 56), trans-dichlorobis(triphenylphosphine) palladium (II) (0.009 g, 0.013 mmol), 2 M sodium carbonate (0.20 mL) and 1,2-dimethoxyethane (5 mL) for 18 hours. Cool to ambient temperature, dilute with ethyl acetate and wash with saturated sodium bicarbonate, saturated sodium chloride, dry with magnesium sulfate, filter and remove solvents under reduced pressure. Purify on silica gel with dichloromethane/methanol mixtures to provide the title compound (0.084 g). MS(ES+): m/z=620.1 (M+H)+

후처리

  1. temperatureReflux
  2. washwash with saturated sodium bicarbonate, saturated sodium chloride
  3. dry with materialdry with magnesium sulfate
  4. filtrationfilter
  5. customremove solvents under reduced pressure
  6. customPurify on silica gel with dichloromethane/methanol

출처 및 근거

ORD 기록
ord-d9a1b0db37434476ad9966d0cc4152a0
출처 데이터셋
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07320995B2

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