1-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[3-(3-furanyl)-1-piperazinyl]-3-quinolinecarboxylic acid

HRID 2165673Notes

Reaction equation

HRID 2165673 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]2[NH:11][CH2:10][CH2:9][NH:8][CH2:7]2)=[CH:2]1.[CH2:12]([N:14]1[C:23]2[C:18](=[CH:19][C:20]([F:25])=[C:21](F)[CH:22]=2)[C:17](=[O:26])[C:16]([C:27]([OH:29])=[O:28])=[CH:15]1)[CH3:13]>N1C=CC=CC=1>[CH2:12]([N:14]1[C:23]2[C:18](=[CH:19][C:20]([F:25])=[C:21]([N:8]3[CH2:9][CH2:10][NH:11][CH:6]([C:3]4[CH:4]=[CH:5][O:1][CH:2]=4)[CH2:7]3)[CH:22]=2)[C:17](=[O:26])[C:16]([C:27]([OH:29])=[O:28])=[CH:15]1)[CH3:13]

Participants

4

Reactant 2

HCID 8005211-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 197635372-(Furan-3-yl)piperazine

Product 1

HCID 148393941-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[3-(3-furanyl)-1-piperazinyl]-3-quinolinecarboxylic acidYield 32%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 592 mg of 3-(3-furanyl)piperazine, 329 mg of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and 8 ml of pyridine was heated in a pressure bottle at 95°-100° C. for 18 hours and then purified as described in Example 65, giving 160 mg of the desired product, mp 202°-204° C.

Workup

  1. temperaturewas heated in a pressure bottle at 95°-100° C. for 18 hours
  2. custompurified

Sources & evidence

ORD record
ord-23e39c64af55482598a53314bf2e8c2d
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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