Imiquimod → 8-bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9448

反応式

HRID 9448 の反応式
[CH3:1][CH:2]([CH3:18])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:17])[C:7]=2[N:6]=[CH:5]1.[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:19][C:13]1[CH:12]=[CH:11][C:10]2[N:9]=[C:8]([NH2:17])[C:7]3[N:6]=[CH:5][N:4]([CH2:3][CH:2]([CH3:18])[CH3:1])[C:16]=3[C:15]=2[CH:14]=1

参加物

4

反応物 2

HCID 57469ImiquimodHCID 67184N-bromobutanimide

生成物 1

HCID 111745978-bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine収率 22.6%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A solution of 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (30.0 g, 125 mmol) in chloroform (620 mL) was heated to 50° C., and N-bromosuccinimide (28.8 g, 162 mmol) was added in five portions over a period of five minutes. The resulting dark red solution was heated at reflux for 45 minutes, allowed to cool to ambient temperature, and stirred for one hour. A precipitate formed, was isolated by filtration, and was washed with water and diethyl ether to provide 9.0 g of 8-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]-quinolin-4-amine as a solid.

後処理

  1. temperatureThe resulting dark red solution was heated
  2. temperatureat reflux for 45 minutes
  3. customA precipitate formed
  4. customwas isolated by filtration
  5. washwas washed with water and diethyl ether

出典と根拠

ORDレコード
ord-a0aab8bc0b124b31a57accf5057cc740
出典データセット
uspto-grants-2006_08
特許番号
US07091214B2

関連ノート

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