Pyridine → Quinoline carboxamide derivative 1

HRID 1259845

Reaktionsgleichung

[C:1]1([C:7]2[CH:16]=[C:15]([C:17](Cl)=[O:18])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[NH2:26][C:27]1[O:28][C:29]([C:32]2[O:33][CH:34]=[CH:35][CH:36]=2)=[N:30][N:31]=1>CO>[O:33]1[CH:34]=[CH:35][CH:36]=[C:32]1[C:29]1[O:28][C:27]([NH:26][C:17]([C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:16]=2)=[O:18])=[N:31][N:30]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

2-phenyl-4-quinolinecarbonyl chloride (2.00 g, 7.47 mmol) was added in small portions to a pyridine (40 mL) solution of commercially available 2-amino-5-(2-furyl)-1,3,4-oxadiazole (1.69 g, 11.2 mmol), and the mixture was heated with stirring at 60° C. for 6 hours. To the reaction solution, methanol was added, and the solvent was distilled off. The obtained residue was triturated by the addition of water. The deposited crystal was collected by filtration, washed with methanol and then with ethyl acetate, and then recrystallized from DMF-methanol to obtain the title compound (1.23 g, 3.22 mmol) as a light brown powder (yield: 43%).

Aufarbeitung

temperaturethe mixture was heated
distillationthe solvent was distilled off
customThe obtained residue was triturated by the addition of water
filtrationThe deposited crystal was collected by filtration
washwashed with methanol
customwith ethyl acetate, and then recrystallized from DMF-methanol

Quellen und Nachweise

ORD-Eintrag: ord-ee5b437691344d60bdb8eed564e0619d
Quelldatensatz: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08466290B2

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