Acetic Acid → HCID 9829429, compound

HRID 1266171Notes

Reaction equation

[F:1][C:2]1[C:29]([N:30]2[CH2:35][CH2:34][N:33]([C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)[CH2:32][CH2:31]2)=[C:28]([F:43])[C:5]2=[N:6][C:7]3[N:8]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=4[F:27])[CH:9]=[C:10]([C:15]([O:17]CC)=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1.C(O)(=O)C>C(O)C.[OH-].[K+]>[F:1][C:2]1[C:29]([N:30]2[CH2:31][CH2:32][N:33]([C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)[CH2:34][CH2:35]2)=[C:28]([F:43])[C:5]2=[N:6][C:7]3[N:8]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=4[F:27])[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: 80 °C

Procedure

A suspension of 1.2 g of ethyl 7,9-difluoro-1-(2,4-difluorophenyl)-8-[4-(4-fluorophenyl)piperazin-1-yl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate in 15 cm3 of ethanol and 16 cm3 of 1N aqueous potassium hydroxide solution was heated with stirring at a temperature around 80° C. for 2 hours. 10 cm3 of a 10% aqueous acetic acid solution were added, at approximately 80° C., to the solution obtained. The insoluble material was filtered off at this temperature, washed 2 times with 30 cm3 of water and recrystallized from a mixture of 12.5 cm3 of ethanol and 12.5 cm3 of dimethylformamide. 0.75 g of 7,9-difluoro-1-(2,4-difluorophenyl)-8-[4-(4-fluorophenyl)piperazin-1-yl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid was obtained in the form of a yellow solid melting at about 284-286° C.

Workup

temperaturewas heated
customobtained
filtrationThe insoluble material was filtered off at this temperature
washwashed 2 times with 30 cm3 of water
customrecrystallized from a mixture of 12.5 cm3 of ethanol and 12.5 cm3 of dimethylformamide

Sources & evidence

ORD record: ord-abdd68c9a81d409f894976cdd0ad8daa
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548506B2

Reaction notes

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