7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 1-Ethyl-6-fluoro-1,4-dihydro-7-[3-(3-methyl-2-thienyl)-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid

HRID 248469Notes

Reaction equation

HRID 248469 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]1[CH2:12][NH:11][CH2:10][CH2:9][NH:8]1.Cl[C:14]1[CH:23]=[C:22]2[C:17]([C:18](=[O:29])[C:19]([C:26]([OH:28])=[O:27])=[CH:20][N:21]2[CH2:24][CH3:25])=[CH:16][C:15]=1[F:30]>N1C=CC=CC=1>[CH2:24]([N:21]1[C:22]2[C:17](=[CH:16][C:15]([F:30])=[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH:7]([C:3]4[S:4][CH:5]=[CH:6][C:2]=4[CH3:1])[CH2:12]3)[CH:23]=2)[C:18](=[O:29])[C:19]([C:26]([OH:28])=[O:27])=[CH:20]1)[CH3:25]

Participants

4

Reactant 2

HCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 197635922-(3-Methylthiophen-2-YL)piperazine

Product 1

HCID 148393591-Ethyl-6-fluoro-1,4-dihydro-7-[3-(3-methyl-2-thienyl)-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 3.64 g portion of 2-(3-methyl-2-thienyl)piperazine was added to 10 ml of pyridine followed by 1.35 g of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid. The mixture was placed in a pressure bottle, under argon, sealed and heated at 120°-130° C., with stirring for 18 hours. The solvent was removed and the residue purified by chromatography, eluting with chloroform:methanol (9:1), giving 135 mg of the desired product, mp 252°-255° C. (dec.).

Workup

  1. customsealed
  2. temperatureheated at 120°-130° C.
  3. customThe solvent was removed
  4. customthe residue purified by chromatography
  5. washeluting with chloroform:methanol (9:1)

Sources & evidence

ORD record
ord-8f9e7cf2fc2a457e890a86bef5669222
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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