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 triethylamine salt

HRID 1415939

Reaction equation

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].Cl.Cl.[NH2:33][C@H:34]1[CH2:38][CH2:37][NH:36][CH2:35]1.[CH2:39]([N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[CH3:40]>C(O)C>[CH:34]([O:27][CH:18]([CH3:17])[CH3:19])([CH3:38])[CH3:35].[CH2:39]([N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[CH3:40].[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:36]4[CH2:37][CH2:38][C@H:34]([NH2:33])[CH2:35]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]

Participants

Conditions

Temperature: 90 °C

Procedure

To 1,000 mg of N,N-dimethylformamide were added 220 mg of 1-(3-amino-4,6-difluorophenyl)-7-chloro-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid, 210 mg of (3S)-3-aminopyrrolidine dihydrochloride, and 400 mg of triethylamine. The solution was stirred at 90° C. for 1.5 hours. The reaction solution was allowed to cool down, combined with 10 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 220 mg of the title compound.

Workup

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

Sources & evidence

ORD record: ord-8325b659aecf44de9f6a0364c03a3721
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05910498

Linked notes

Loading…