4-Aminopyridine → 2-{2-[7-Chloro-2-oxo-6-(3-pyridin-4-yl-ureido)-3-thiophen-2-yl-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1858168

Reaktionsgleichung

[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:28])=[C:24]([NH2:27])[CH:25]=2)[NH:20][C:19](=[O:29])[C:18]=1[C:30]1[S:31][CH:32]=[CH:33][CH:34]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:35](Cl)(Cl)=[O:36].C(N(CC)CC)C.[NH2:46][C:47]1[CH:52]=[CH:51][N:50]=[CH:49][CH:48]=1>C(Cl)Cl.C(OCC)(=O)C>[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:28])=[C:24]([NH:27][C:35]([NH:46][C:47]3[CH:52]=[CH:51][N:50]=[CH:49][CH:48]=3)=[O:36])[CH:25]=2)[NH:20][C:19](=[O:29])[C:18]=1[C:30]1[S:31][CH:32]=[CH:33][CH:34]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of 2-[2-(6-amino-7-chloro-2-oxo-3-thiophen-2-yl-1,2-dihydroquinolin-4-yloxy)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester in dry methylene chloride at 0° C. is added phosgene followed by an excess of triethylamine and the mixture stirred for 1 hour at 0° C. At this time, 4-aminopyridine is added and the mixture allowed to warm to room temperature. Upon completion of the reaction, the mixture is diluted with ethyl acetate and the mixture quenched by the addition of 10% citric acid. The organic portion is concentrated in vacuo to provide the crude title compound.

Aufarbeitung

temperatureto warm to room temperature
customUpon completion of the reaction
customthe mixture quenched by the addition of 10% citric acid
concentrationThe organic portion is concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-f141dfdc86484615a08f43259d6a56d3
Quelldatensatz: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06150522

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