Diisopropylethylamine → Gsk163090

HRID 15822노트

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HRID 15822 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 11292933Gsk163090수율 70%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
75 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-af166f26abae404db23b390200021af7
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732600B2

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