Methanol → 5-Amino-1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

HRID 369311Notes

Reaction equation

[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([Cl:14])=[C:8]2[C:3]=1[C:4](=[O:27])[C:5]([C:24]([OH:26])=[O:25])=[CH:6][N:7]2[C:15]1[C:20]([F:21])=[CH:19][C:18]([F:22])=[C:17]([NH2:23])[N:16]=1.[CH3:28][OH:29].C[O-].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([O:29][CH3:28])[C:9]([Cl:14])=[C:8]2[C:3]=1[C:4](=[O:27])[C:5]([C:24]([OH:26])=[O:25])=[CH:6][N:7]2[C:15]1[C:20]([F:21])=[CH:19][C:18]([F:22])=[C:17]([NH2:23])[N:16]=1

Participants

Conditions

Temperature: 45 °C

Procedure

5-Amino-1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (150 mg) and a methanol solution (about 28%; 200 mg) of sodium methoxide were added to methanol (2 ml), and the mixture was stirred at 45° C. for 3 days. Acetic acid (80 mg) was added to the reaction mixture, and the mixture was heated under reflux for 1 hour. After the reaction mixture was allowed to cool, deposits were collected by filtration and washed with methanol and diisopropyl ether in that order to obtain the title compound (122 mg) as a yellow powder.

Workup

temperaturethe mixture was heated
temperatureunder reflux for 1 hour
temperatureto cool
filtrationdeposits were collected by filtration
washwashed with methanol and diisopropyl ether in that order

Sources & evidence

ORD record: ord-e0c466a7e3ab4db594e3da2eedbef9e9
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136823

Reaction notes

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