Diisopropylethylamine → HCID 57444322、化合物

HRID 15833ノート

反応式

HRID 15833 の反応式
C(N(CC)C(C)C)(C)C.[CH3:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[C:14]([F:27])[CH:15]=[CH:16][C:17]=2[N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[N:12]=1.CS(O[CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([N+:41]([O-:43])=[O:42])[CH:36]=1)(=O)=O>CN(C)C=O>[F:27][C:14]1[CH:15]=[CH:16][C:17]([N:21]2[CH2:26][CH2:25][N:24]([CH2:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([N+:41]([O-:43])=[O:42])[CH:36]=3)[CH2:23][CH2:22]2)=[C:18]2[C:13]=1[N:12]=[C:11]([CH3:10])[CH:20]=[CH:19]2

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 219738843-Nitrophenethyl methanesulfonateHCID 574443218-Fluoro-2-methyl-5-piperazin-1-yl-quinoline

生成物 1

HCID 57444322HCID 57444322、化合物収率 46%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

N,N-Diisopropylethylamine (0.25 mL; 3 eq) was added to a solution of 2-methyl-5-(1-piperazinyl)-8-fluoro quinoline (0.170 g; 1 eq) and 2-(3-nitrophenyl)ethyl methanesulfonate (D4) (0.17 g; 1 eq) in dimethylformamide (4.0 mL). The reaction mixture was heated to 100° C. for 10 hours. The dark solution was cooled to room temperature and concentrated under reduced pressure. The residue was diluted with water (3 mL) and brine (1 mL) and extracted into ethyl acetate (3×3 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The crude was purified by flash chromatography on silica gel, eluting with a gradient from dichloromethane to dichloromethane-methanol (98:2) affording the title compound in 46% yield (0.126 g).

後処理

  1. temperatureThe dark solution was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with water (3 mL) and brine (1 mL)
  4. extractionextracted into ethyl acetate (3×3 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by flash chromatography on silica gel
  8. washeluting with a gradient from dichloromethane to dichloromethane-methanol (98:2)

出典と根拠

ORDレコード
ord-9125748467914a7fb21ad5afe123e231
出典データセット
uspto-grants-2010_06
特許番号
US07732600B2

反応ノート

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