Water → RP60556A

HRID 1266154Notes

Reaction equation

[F:1][C:2]1[C:20](F)=[CH:19][C:5]2=[N:6][C:7]3[N:8]([CH3:18])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:25][CH:24]=1.O>CS(C)=O>[F:1][C:2]1[C:20]([N:32]2[CH2:31][CH2:30][N:29]([C:26]3[CH:25]=[CH:24][C:23]([F:22])=[CH:28][CH:27]=3)[CH2:34][CH2:33]2)=[CH:19][C:5]2=[N:6][C:7]3[N:8]([CH3:18])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of 5.0 g of 7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid and 6.2 g of 4-(4-fluorophenyl)-piperazine in 30 cm3 of dimethyl sulphoxide was heated, with stirring, at a temperature around 90° C. for approximately 4 hours. After cooling to approximately 20° C., 25 cm3 of water were added to the reaction mixture. The insoluble material was filtered off and washed with 2 times 25 cm3 of water. After recrystallizing once from 150 cm3 of dimethylformamide, 7.6 g of 7-fluoro-8-[4-(4-fluorophenyl)piperazin-1-yl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid were obtained in the form of a yellow solid melting at about 318-9° C.

Workup

temperaturewas heated
temperatureAfter cooling to approximately 20° C.
filtrationThe insoluble material was filtered off
washwashed with 2 times 25 cm3 of water
customAfter recrystallizing once from 150 cm3 of dimethylformamide

Sources & evidence

ORD record: ord-92877b8edf304faab44a96aeb48c1572
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548506B2

Reaction notes

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