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Propylamine → 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-6-pyrazin-2-ylethynyl-1,2-dihydroquinolin4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1858102
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인쇄 미리보기

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HRID 1858102 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:29])=[C:24]([C:27]#[CH:28])[CH:25]=2)[NH:20][C:19](=[O:30])[C:18]=1[C:31]1[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([CH3:38])[CH:32]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N)CC.Cl[C:44]1[CH:49]=[N:48][CH:47]=[CH:46][N:45]=1>C(OCC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:29])=[C:24]([C:27]#[C:28][C:44]3[CH:49]=[N:48][CH:47]=[CH:46][N:45]=3)[CH:25]=2)[NH:20][C:19](=[O:30])[C:18]=1[C:31]1[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([CH3:38])[CH:32]=1)=[O:7])([CH3:3])([CH3:2])[CH3:4]
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참가 물질

7

반응물 3

HCID 7852PropylamineHCID 73277ChloropyrazineHCID 544333822-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-ethynyl-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 538220492-{2-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-6-pyrazin-2-ylethynyl-1,2-dihydroquinolin4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 178418397HCID 178418397, 화합물촉매
HCID 3283Diethyl Ether용매

반응 조건

온도
90 °C

실험 절차

To a solution of 2-{2-[7-chloro-3-(3,5-dimethylphenyl)-6-ethynyl-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (123 mg in 1.5 mL N,N-dimethylformamide) was added tetrakis(triphenylphosphine)palladium (13 mg) followed by copper(I) iodide (22 mg), n-propylamine (0.19 mL) and chloropyrazine (0.026 mL) and the mixture heated to 90° C. on an oil bath. After 10 minutes, the mixture was cooled to room temperature, diluted with diethyl ether and washed successively with water and brine then dried over magnesium sulfate. Purification of the concentrate by flash chromatography on silica gel (ethyl acetate:hexane, 30:70; then 40:60; then 50:50) gave the title compound (69 mg).

후처리

  1. temperaturethe mixture was cooled to room temperature
  2. washwashed successively with water and brine
  3. dry with materialthen dried over magnesium sulfate
  4. customPurification of the
  5. concentrationconcentrate by flash chromatography on silica gel (ethyl acetate

출처 및 근거

ORD 기록
ord-8e675d90508142e18e78202e840c1a23
출처 데이터셋
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06150352

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