Pyrrolidine → 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(3-oxo-3-pyrrolidin-1-yl-propyl)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1858097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1858097
[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:32])=[C:24]([CH2:27][CH2:28][C:29]([OH:31])=O)[CH:25]=2)[NH:20][C:19](=[O:33])[C:18]=1[C:34]1[CH:39]=[C:38]([CH3:40])[CH:37]=[C:36]([CH3:41])[CH:35]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)[CH2:45][CH2:46][CH2:47][N:48]=[C:49]=NCC.ON1C2C=CC=CC=2N=N1.N1CCCC1>>[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:32])=[C:24]([CH2:27][CH2:28][C:29](=[O:31])[N:48]3[CH2:49][CH2:45][CH2:46][CH2:47]3)[CH:25]=2)[NH:20][C:19](=[O:33])[C:18]=1[C:34]1[CH:39]=[C:38]([CH3:40])[CH:37]=[C:36]([CH3:41])[CH:35]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 4

HCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 538441682-{2-[6-(2-Carboxyethyl)-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 536595522-{2-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(3-oxo-3-pyrrolidin-1-yl-propyl)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl esterAusbeute 55 %

Versuchsvorschrift

To a solution of 2-{2-[6-(2-carboxyethyl)-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (15 mg in 0.5 mL of dry methylene chloride) was added 8.0 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) followed by 5.2 mg 1-hydroxybenzotriazole (HOBt) and the mixture stirred for 10 minutes. At this time, 9.2 mg of pyrrolidine was added and the reaction allowed to proceed at room temperature. After 40 minutes, the mixture was concentrated in vacuo and purified by flash chromatography on silica gel (methylene chloride: 10% ammonium hydroxide in methanol, 95:5; then 90:10) to give the title compound (9 mg).

Aufarbeitung

  1. customto proceed at room temperature
  2. waitAfter 40 minutes
  3. concentrationthe mixture was concentrated in vacuo
  4. custompurified by flash chromatography on silica gel (methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-09208c2a8eb443b8b969f9c65b382b01
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06150352

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