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Dimethylformamide → 4-{1-[2-(2-methoxy-ethoxy)-ethyl]-1H-benzoimidazol-2-yl}-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 2230711
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HRID 2230711 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)C=O.[H-].[Na+].Br[CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38]>O>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:16]([CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38])[C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 1235321-Bromo-3,6-dioxaheptaneHCID 184646551-t-butoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane

생성물 1

HCID 701494634-{1-[2-(2-methoxy-ethoxy)-ethyl]-1H-benzoimidazol-2-yl}-[1,4]diazepane-1-carboxylic acid tert-butyl ester수율 93.8%

시약·촉매·용매 1

HCID 962
Water
용매

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온도
70 °C

실험 절차

Treat a solution of 1-(t-butoxycarbonyl)-4-(1H-benzimidazol-2-yl)[1,4]diazepan (preparation 9, 0.50 g, 1.58 mmol) and dimethylformamide (10 mL) with sodium hydride (0.083 g, 2.08 mmol, 60% dispersion in oil) at room temperature. After 30 minutes, add 1-bromo-2-(2-methoxyethoxy)ethane (0.34 g, 1.88 mmol, Aldrich Chemical Company) and heat two hours at 70° C. Cool the reaction, add water (10 mL) and extract with dichloromethane (100 mL). Wash the organic phase with water, dry (Na2SO4), filter and concentrate the filtrate to afford 4-{1-[2-(2-methoxy-ethoxy)-ethyl]-1H-benzoimidazol-2-yl}-[1,4]diazepane-1-carboxylic acid tert-butyl ester (0.62 g).

후처리

  1. temperatureCool
  2. customthe reaction
  3. extractionextract with dichloromethane (100 mL)
  4. washWash the organic phase with water
  5. dry with materialdry (Na2SO4)
  6. filtrationfilter
  7. concentrationconcentrate the filtrate

출처 및 근거

ORD 기록
ord-963b44c8d2c549bc8b0ed15545560701
출처 데이터셋
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06423704B1

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