Chloroform → 1-(3-Benzoylamino-4,6-difluorophenyl)-7-chloro-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

HRID 1415935

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:21])=[C:17]([Cl:20])[N:18]=3)[C:13](=[O:22])[C:12]([C:23]([OH:25])=[O:24])=[CH:11]2)[C:5]([F:9])=[CH:6][C:7]=1[F:8].CN(C)C=O.[C:31](O[C:40](=[O:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)(=O)[C:32]1C=CC=C[CH:33]=1.C(Cl)(Cl)Cl>O>[CH:32]([O:22][CH:13]([CH3:12])[CH3:14])([CH3:33])[CH3:31].[C:40]([NH:1][C:2]1[CH:3]=[C:4]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:21])=[C:17]([Cl:20])[N:18]=3)[C:13](=[O:22])[C:12]([C:23]([OH:25])=[O:24])=[CH:11]2)[C:5]([F:9])=[CH:6][C:7]=1[F:8])(=[O:47])[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

Conditions

Temperature: 100 °C

Procedure

1-(3-amino-4,6-difluorophenyl)-7-chloro-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid (310 mg) was added to 920 mg of N,N-dimethylformamide together with 220 mg of benzoic anhydride, which was stirred at 70° C. for 2 hours and at 100° C. for 2.5 hours. The reaction solution was combined with 50 ml of chloroform and 150 ml of distilled water. The solution was separated, the chloroform layer was dried over anhydrous magnesium sulfate and concentrated in vacua. Ethanol (6 ml) was added to the residue, which was allowed to stand. The precipitate was collected by filtration and washed with ethanol and then with diisopropyl ether to give 184 mg of the title compound.

Workup

customThe solution was separated
dry with materialthe chloroform layer was dried over anhydrous magnesium sulfate
concentrationconcentrated in vacua
additionEthanol (6 ml) was added to the residue, which
filtrationThe precipitate was collected by filtration
washwashed with ethanol

Sources & evidence

ORD record: ord-5903198be8b94c9f9f8299525f10c662
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05910498

Linked notes

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