1-Cyclopropyl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 1-Cyclopropyl-5,6,8-trifluoro-7-(3-fluoromethyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 477015Notes

Reaction equation

HRID 477015 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([F:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.[F:22][CH2:23][CH:24]1[CH2:29][NH:28][CH2:27][CH2:26][NH:25]1>O1CCOCC1>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([F:17])[C:10]([F:16])=[C:11]([N:28]4[CH2:27][CH2:26][NH:25][CH:24]([CH2:23][F:22])[CH2:29]4)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 138255151-Cyclopropyl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 14479501HCID 14479501, compound

Product 1

HCID 143045991-Cyclopropyl-5,6,8-trifluoro-7-(3-fluoromethyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In the same manner as described in Example 1, a mixture of 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro4-oxoquinoline-3-carboxylic acid, 2-fluoromethylpiperazine, and dioxane was refluxed for 5 hours to give 1-cyclopropyl-5,6,8-trifluoro-7-(3-fluoromethyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, which was recrystallized from chloroform, m.p. 219°-220° C.

Workup

  1. temperaturewas refluxed for 5 hours

Sources & evidence

ORD record
ord-85e7c13d976549a6b1e98ee2c221926a
Source dataset
uspto-grants-1989_12
Patent number
US04886810

Reaction notes

Loading…