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 1858168Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-f141dfdc86484615a08f43259d6a56d3
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150522

Reaction notes

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