Dimethylformamide → 1-(3-amino-4,6-difluorophenyl)-7-[(3S)-3-aminopyrrolidin-1-yl]-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

HRID 1415938

Reaktionsgleichung

CN(C)C=O.[NH2:6][C:7]1[CH:8]=[C:9]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([F:26])=[C:22](Cl)[N:23]=3)[C:18](=[O:27])[C:17]([C:28]([OH:30])=[O:29])=[CH:16]2)[C:10]([F:14])=[CH:11][C:12]=1[F:13].[NH2:31][C@H:32]1[CH2:36][CH2:35][NH:34][CH2:33]1.C(N(CC)CC)C>C(O)C>[CH:32]([O:27][CH:18]([CH3:17])[CH3:19])([CH3:36])[CH3:33].[NH2:6][C:7]1[CH:8]=[C:9]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([F:26])=[C:22]([N:34]4[CH2:35][CH2:36][C@H:32]([NH2:31])[CH2:33]4)[N:23]=3)[C:18](=[O:27])[C:17]([C:28]([OH:30])=[O:29])=[CH:16]2)[C:10]([F:14])=[CH:11][C:12]=1[F:13]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

To 6,500 mg of N,N-dimethylformamide were added 1,300 mg of 1-(3-amino-4,6-difluorophenyl)-7-chloro-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid, 600 mg of (3S)-3-aminopyrrolidine, and 1,000 mg of triethylamine. The solution was stirred at 90° C. for 1 hour. The reaction solution was allowed to cool down, combined with 25 ml of ethanol, heated at reflux for 5 minutes, and allowed to cool down. The precipitate was collected by filtration and washed with ethanol and then with diisopropyl ether to give 1,410 mg of the title compound.

Aufarbeitung

temperatureto cool down
temperatureheated
temperatureat reflux for 5 minutes
temperatureto cool down
filtrationThe precipitate was collected by filtration
washwashed with ethanol

Quellen und Nachweise

ORD-Eintrag: ord-b023eee62d134e96bb708fa16541416f
Quelldatensatz: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05910498

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