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Triethylamine → tert-butyl [4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-ylmethyl)benzyl]carbamate

HRID 9491
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HRID 9491 반응식
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]1[CH:28]=[CH:27][C:17]([CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:16][CH:15]=1)=[CH:9][CH:8]=[C:7]([Br:29])[CH:6]=2.C(N(CC)CC)C.[CH2:37]([O:39][CH2:40][C:41](Cl)=O)[CH3:38]>ClCCl>[C:22]([O:21][C:20](=[O:26])[NH:19][CH2:18][C:17]1[CH:27]=[CH:28][C:14]([CH2:13][N:12]2[C:11]3[C:10]4[CH:9]=[CH:8][C:7]([Br:29])=[CH:6][C:5]=4[N:4]=[CH:3][C:2]=3[N:1]=[C:38]2[CH2:37][O:39][CH2:40][CH3:41])=[CH:15][CH:16]=1)([CH3:24])([CH3:25])[CH3:23]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 84189Ethoxyacetyl chlorideHCID 21984367Tert-butyl {4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]benzyl}carbamate

생성물 1

HCID 86593767tert-butyl [4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-ylmethyl)benzyl]carbamate수율 35%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-Butyl {4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]benzyl}carbamate (8.46 g, 18.5 mmol), triethylamine (2.25 mL) and dichloromethane (92 mL) were combined. Ethoxyacetyl chloride (2.92 g, 24 mmol) was added dropwise to the mixture. The reaction was stirred for an additional 1.5 hours and then concentrated under reduced pressure. Ethanol (92 mL) and triethylamine (10.31 mL) were added to the residue and the reaction was heated at reflux temperature for 1.5 hours. A precipitate formed. The reaction was cooled to room temperature and then concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed sequentially with water and saturated aqueous sodium chloride. The organic fraction was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. An initial purification by flash column chromatography eluting with a gradient of CMA in chloroform (2–10%) was followed by recrystallization from acetonitrile to provide 3.4 g of tert-butyl[4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-ylmethyl)benzyl]carbamate as yellow-orange crystals.

후처리

  1. concentrationconcentrated under reduced pressure
  2. additionEthanol (92 mL) and triethylamine (10.31 mL) were added to the residue
  3. temperaturethe reaction was heated
  4. temperatureat reflux temperature for 1.5 hours
  5. customA precipitate formed
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in dichloromethane
  8. washwashed sequentially with water and saturated aqueous sodium chloride
  9. dry with materialThe organic fraction was dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customAn initial purification by flash column chromatography
  13. washeluting with a gradient of CMA in chloroform (2–10%)
  14. customwas followed by recrystallization from acetonitrile

출처 및 근거

ORD 기록
ord-8944d4bc581b4c2091b717fc29f8e6a3
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07091214B2

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