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

HRID 9366

反応式

HRID 9366 の反応式
[CH2:1]([N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:18])[C:8]=2[N:7]=[CH:6]1)[CH:2]([CH3:4])[CH3:3].[Br:19]Br>C(O)(=O)C>[Br:19][C:14]1[CH:13]=[CH:12][C:11]2[N:10]=[C:9]([NH2:18])[C:8]3[N:7]=[CH:6][N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:17]=3[C:16]=2[CH:15]=1

参加物

4

反応物 2

HCID 24408BromineHCID 57469Imiquimod

生成物 1

HCID 111745978-bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine収率 25.6%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine (10.0 g, 41.6 mmol) in acetic acid (150 mL) was added Br2 (10.0 g, 62.6 mmol), and after 24 h, the resulting solid was collected by filtration and washed with H2O. The orange solid was suspended in a saturated aqueous solution of NaHSO3, after which it was again collected and stirred with a 2 M solution of Na2CO3 for 18 h. The solid was collected by filtration, washed with H2O, and azeotropically dried with toluene on a rotary evaporator. Purification on silica gel (7%–10% methanol in CH2Cl2 gradient) afforded 3.4 g of 8-bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine.

後処理

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with H2O
  3. customafter which it was again collected
  4. filtrationThe solid was collected by filtration
  5. washwashed with H2O
  6. dry with materialazeotropically dried with toluene on a rotary evaporator
  7. customPurification on silica gel (7%–10% methanol in CH2Cl2 gradient)

出典と根拠

ORDレコード
ord-ed8f627f3e2042acae8a94dcfcac827a
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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