1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid → 1-Cyclopropyl-6-fluoro-7-[3-(trifluoromethyl)-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 248541Notes

Reaction equation

[F:1][C:2]([F:10])([F:9])[CH:3]1[CH2:8][NH:7][CH2:6][CH2:5][NH:4]1.[CH:11]1([N:14]2[C:23]3[C:18](=[CH:19][C:20]([F:25])=[C:21](F)[CH:22]=3)[C:17](=[O:26])[C:16]([C:27]([OH:29])=[O:28])=[CH:15]2)[CH2:13][CH2:12]1>N1C=CC=CC=1>[CH:11]1([N:14]2[C:23]3[C:18](=[CH:19][C:20]([F:25])=[C:21]([N:7]4[CH2:6][CH2:5][NH:4][CH:3]([C:2]([F:10])([F:9])[F:1])[CH2:8]4)[CH:22]=3)[C:17](=[O:26])[C:16]([C:27]([OH:29])=[O:28])=[CH:15]2)[CH2:12][CH2:13]1

Participants

Conditions

Temperature: 77 °C

Procedure

A 0.55 g portion of 2-(trifluoromethyl)piperazine was dissolved in 14 ml of pyridine. To this was added 265 mg of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid. The mixture was stirred for 3 hours at 77° C.. The pyridine was removed by repeated evaporation with toluene. The residue was triturated with hot methanol. The resulting solid was collected, washed with methanol and ether and dried, giving 105 mg of the desired product as a colorless solid.

Workup

customThe pyridine was removed
customevaporation with toluene
customThe residue was triturated with hot methanol
customThe resulting solid was collected
washwashed with methanol and ether
customdried

Sources & evidence

ORD record: ord-bd8ffc8200004476b67fedaae80e53b4
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05210193

Reaction notes

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