7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 14839360, compound

HRID 248470Notes

Reaction equation

HRID 248470 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]3[CH2:15][NH:14][CH2:13][CH2:12][NH:11]3)=[CH:7][C:6]=2[CH:16]=1.Cl[C:18]1[CH:27]=[C:26]2[C:21]([C:22](=[O:33])[C:23]([C:30]([OH:32])=[O:31])=[CH:24][N:25]2[CH2:28][CH3:29])=[CH:20][C:19]=1[F:34]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]3[NH:11][CH2:12][CH2:13][N:14]([C:18]4[CH:27]=[C:26]5[C:21]([C:22](=[O:33])[C:23]([C:30]([OH:32])=[O:31])=[CH:24][N:25]5[CH2:28][CH3:29])=[CH:20][C:19]=4[F:34])[CH2:15]3)=[CH:7][C:6]=2[CH:16]=1

Participants

4

Reactant 2

HCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 19932965HCID 19932965, compound

Product 1

HCID 14839360HCID 14839360, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 1.45 g portion of 2-(5-chloro-2-benzofuranyl)piperazine was added to 5 ml of pyridine. A 540 mg portion of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid was added and the mixture was heated in a sealed bottle, under argon, at 130°-135° C. for 18 hours, then cooled in an ice bath. The solid was collected, triturated with cold pyridine, dichloromethane, ether and dimethylformamide, giving 180 mg of the desired product, mp 262°-263° C.

Workup

  1. temperaturethe mixture was heated in a sealed bottle, under argon, at 130°-135° C. for 18 hours
  2. temperaturecooled in an ice bath
  3. customThe solid was collected
  4. customtriturated with cold pyridine, dichloromethane, ether and dimethylformamide

Sources & evidence

ORD record
ord-13b92961cf6d4856abfba368e6106be5
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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