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

HRID 9366

반응식

HRID 9366 반응식
[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

참가 물질

4

반응물 2

HCID 24408BromineHCID 57469Imiquimod

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ed8f627f3e2042acae8a94dcfcac827a
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091214B2

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