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Diisopropylethylamine → 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid 2-trimethylsilanylethyl ester

HRID 1858076
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HRID 1858076 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:21][CH2:22][CH2:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][NH:25]3)=[C:7]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[N+:30]([O-:32])=[O:31].[C:33](=O)([O:41]C1C=CC([N+]([O-])=O)=CC=1)[O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38].C(N(C(C)C)CC)(C)C>>[CH3:38][Si:37]([CH3:40])([CH3:39])[CH2:36][CH2:35][O:34][C:33]([N:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH:24]1[CH2:23][CH2:22][O:21][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[C:3]([N+:30]([O-:32])=[O:31])[CH:4]=2)[NH:9][C:8](=[O:12])[C:7]=1[C:13]1[CH:14]=[C:15]([CH3:20])[CH:16]=[C:17]([CH3:19])[CH:18]=1)=[O:41]
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참가 물질

4

반응물 3

HCID 81531DiisopropylethylamineHCID 30861164-Nitrophenyl 2-(trimethylsilyl)ethyl carbonateHCID 221245137-chloro-3-(3,5-dimethylphenyl)-6-nitro-4-(2-piperidin-2-yl-ethoxy)-1H-quinolin-2-one

생성물 1

HCID 539966322-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid 2-trimethylsilanylethyl ester수율 69.5%

실험 절차

To a solution of 7-chloro-3-(3,5-dimethylphenyl)-6-nitro-4-(2-piperidin-2-yl-ethoxy)-1H-quinolin-2-one (200 mg in 5 mL dicloroethane) was added 136 mg of 2-(trimethylsilyl)ethyl 4-nitrophenyl carbonate followed by 0.092 mL diisopropylethylamine and the mixture heated to reflux. After 20 hours, the reaction was cooled to room temperature, concentrated in vacuo and purified by flash chromatography on silica gel (ethyl acetate:hexane, 1:1) to give the title compound (183 mg.)

후처리

  1. temperaturethe mixture heated to reflux
  2. concentrationconcentrated in vacuo
  3. custompurified by flash chromatography on silica gel (ethyl acetate:hexane, 1:1)

출처 및 근거

ORD 기록
ord-0ea4e2d319264667830ec9f4f8c2e71f
출처 데이터셋
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06150352

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