7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 14839367, compound

HRID 2165624Notes

Reaction equation

HRID 2165624 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[CH2:11][NH:10][CH2:9][CH2:8][NH:7]1.Cl[C:13]1[CH:22]=[C:21]2[C:16]([C:17](=[O:28])[C:18]([C:25]([OH:27])=[O:26])=[CH:19][N:20]2[CH2:23][CH3:24])=[CH:15][C:14]=1[F:29]>N1C=CC=CC=1>[CH2:23]([N:20]1[C:21]2[C:16](=[CH:15][C:14]([F:29])=[C:13]([N:10]3[CH2:9][CH2:8][NH:7][CH:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)[CH2:11]3)[CH:22]=2)[C:17](=[O:28])[C:18]([C:25]([OH:27])=[O:26])=[CH:19]1)[CH3:24]

Participants

4

Reactant 2

HCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 27717262-Thiophen-2-yl-piperazine

Product 1

HCID 14839367HCID 14839367, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 504 mg of the above piperazine, 269 mg of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and 10 ml of pyridine was refluxed under argon for 24 hours, then cooled and evaporated under reduced pressure. The residue was triturated with ether, the solid collected, dissolved in 40% acetic acid and neutralized with 1N sodium hydroxide. The solid was collected, washed with methanol, ether and dried, giving 110 mg of the desired product, mp 232°-234° C.

Workup

  1. temperaturewas refluxed under argon for 24 hours
  2. temperaturecooled
  3. customevaporated under reduced pressure
  4. customThe residue was triturated with ether
  5. customthe solid collected
  6. dissolutiondissolved in 40% acetic acid and neutralized with 1N sodium hydroxide
  7. customThe solid was collected
  8. washwashed with methanol, ether
  9. customdried

Sources & evidence

ORD record
ord-32e51ed76fec454bb16a1a8be8392a3f
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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