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Cesium carbonate → 2-((1H-indol-3-yl)methyl)-9-(quinolin-3-yl)-2,9-diazaspiro[5.5]undecan-1-one

HRID 41575
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HRID 41575 반응식
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([N:11]2[CH2:42][CH2:41][C:14]3([C:19](=[O:20])[N:18]([CH2:21][C:22]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[N:24](S(C5C=CC(C)=CC=5)(=O)=O)[CH:23]=4)[CH2:17][CH2:16][CH2:15]3)[CH2:13][CH2:12]2)[CH:2]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CO.C(OCC)(=O)C>[NH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]([CH2:21][N:18]2[CH2:17][CH2:16][CH2:15][C:14]3([CH2:13][CH2:12][N:11]([C:3]4[CH:2]=[N:1][C:10]5[C:5]([CH:4]=4)=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH2:42][CH2:41]3)[C:19]2=[O:20])=[CH:23]1
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참가 물질

5

반응물 2

HCID 10796Cesium carbonateHCID 672511379-(quinolin-3-yl)-2-((1-tosyl-1H-indol-3-yl)methyl)-2,9-diazaspiro[5.5]undecan-1-one

생성물 1

HCID 532597892-((1H-indol-3-yl)methyl)-9-(quinolin-3-yl)-2,9-diazaspiro[5.5]undecan-1-one수율 73%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

The mixture of 9-(quinolin-3-yl)-2-((1-tosyl-1H-indol-3-yl)methyl)-2,9-diazaspiro[5.5]undecan-1-one (60 mg, 0.1 mmol) and Cs2CO3 (150 mg, 0.46 mmol) in methanol (2 mL) was heated under reflux for 18 h. The reaction mixture was diluted with ethyl acetate and washed with water and brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound (31 mg, 71%). [1H NMR (600 MHz, DMSO-d6) ♀ ppm 10.94 (br. s., 1H), 8.86 (d, 1H), 7.86-7.83 (m, 1H), 7.77-7.75 (m, 1H), 7.56-7.52 (m, 2H), 7.48-7.43 (m, 2H), 7.34 (d, 1H), 7.28 (d, 1H), 7.06 (t, 1H), 6.95 (t, 1H), 4.64 (s, 2H), 3.77-3.68 (m, 2H), 3.19-3.13 (m, 2H), 3.06 (t, 2H), 2.30-2.19 (m, 2H), 1.80-1.72 (m, 2H), 1.72-1.63 (m, 2H), 1.60-1.50 (m, 2H); LCMS RtA=1.05 min, [M+H]+=425.3].

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d3c3c8020636447bb8e77f6cd8fdc980
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08530648B2

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