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Sodium Chloride → 1-[4-amino-2-(2-methoxyethyl)-7-[2-(pyrrol-1-yl)ethoxy]-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

HRID 2383184
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HRID 2383184 반응식
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][CH2:21][O:22][CH3:23])[N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([OH:24])=[CH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:32][CH2:33][N:34]1[CH:38]=[CH:37][CH:36]=[CH:35]1.[Cl-].[Na+]>O>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][CH2:21][O:22][CH3:23])[N:14]([CH2:15][C:16]([CH3:18])([OH:19])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:24][CH2:32][CH2:33][N:34]3[CH:38]=[CH:37][CH:36]=[CH:35]3)=[CH:5][C:4]=2[N:3]=1
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참가 물질

6

반응물 4

HCID 5234Sodium ChlorideHCID 10796Cesium carbonateHCID 116512251-(2-Bromoethyl)pyrroleHCID 1360752004-amino-1-(2-hydroxy-2-methylpropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-7-ol

생성물 1

HCID 575453031-[4-amino-2-(2-methoxyethyl)-7-[2-(pyrrol-1-yl)ethoxy]-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

시약·촉매·용매 1

HCID 962Water용매

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온도
50 °C

실험 절차

4-Amino-1-(2-hydroxy-2-methylpropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-7-ol was alkylated as described in the general procedure for Examples 7-20, using 2 equivalents of cesium carbonate and 1.1 equivalents of 1-(2-bromoethyl)pyrrole. The reaction was heated overnight at 50° C. and then heated to 80° C. for an additional four hours. The reaction was cooled and poured into water containing 20 g of sodium chloride. The resulting precipitate was filtered and purified using column chromatography eluting with a gradient of 0-8% methanol in dichloromethane. The clean fractions were combined, concentrated, and recrystallized from acetonitrile to give 160 mg of 1-[4-amino-2-(2-methoxyethyl)-7-[2-(pyrrol-1-yl)ethoxy]-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as an off-white solid, mp 168.0-169.0° C.

후처리

  1. temperatureheated to 80° C. for an additional four hours
  2. temperatureThe reaction was cooled
  3. filtrationThe resulting precipitate was filtered
  4. custompurified
  5. washeluting with a gradient of 0-8% methanol in dichloromethane
  6. concentrationconcentrated
  7. customrecrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-1c06a2564daf4196b80a39271b5cd4ce
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08263594B2

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