Diisopropylethylamine → Gsk163090

HRID 15822ノート

反応式

HRID 15822 の反応式
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:18][CH2:17][NH:16][C:15]2=[O:19])[CH:9]=1)(=O)=O.[CH3:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[N:22]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[CH3:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[N:31]2[CH2:36][CH2:35][N:34]([CH2:6][CH2:7][C:8]3[CH:9]=[C:10]([N:14]4[CH2:18][CH2:17][NH:16][C:15]4=[O:19])[CH:11]=[CH:12][CH:13]=3)[CH2:33][CH2:32]2)[N:22]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 498519012-Methyl-5-piperazin-1-yl-quinolineHCID 574442972-[3-(2-Oxo-1-imidazolidinyl)phenyl]ethyl methanesulfonate

生成物 1

HCID 11292933Gsk163090収率 70%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
75 °C

実験手順

2-[3-(2-Oxo-1-imidazolidinyl)phenyl]ethyl methanesulfonate (1.32 wt) and 2-methyl-5-(1-piperazinyl)quinoline (1 wt.) were suspended in acetonitrile (5 vol) at room temperature under nitrogen. Diisopropylethylamine (1.53 vol) was added dropwise over 30 minutes, and the mixture was then stirred at 75° C. for 4 hours. The reaction mixture was cooled to room temperature, concentrated to 2 vol, and diluted with ethyl acetate (7 vol). The organic layer was washed with saturated aqueous ammonium chloride solution (2×3 vol), followed by water (1×3 vol). The organic layer was evaporated to dryness, yielding the title compound as a brown foam (70% th).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated to 2 vol
  3. additiondiluted with ethyl acetate (7 vol)
  4. washThe organic layer was washed with saturated aqueous ammonium chloride solution (2×3 vol)
  5. customThe organic layer was evaporated to dryness

出典と根拠

ORDレコード
ord-af166f26abae404db23b390200021af7
出典データセット
uspto-grants-2010_06
特許番号
US07732600B2

反応ノート

読み込み中…