Fluoroquinolonic acid → HCID 23042970, compound

HRID 2165694Notes

Reaction equation

HRID 2165694 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].[C:20]1([S:26]([N:29]2[CH:33]=[CH:32][C:31]([CH:34]3[CH2:39][NH:38][CH2:37][CH2:36][NH:35]3)=[CH:30]2)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>N1C=CC=CC=1>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([N:38]4[CH2:37][CH2:36][NH:35][CH:34]([C:31]5[CH:32]=[CH:33][N:29]([S:26]([C:20]6[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=6)(=[O:28])=[O:27])[CH:30]=5)[CH2:39]4)[CH:11]=3)[C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8]2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 483180Fluoroquinolonic acidHCID 19763567HCID 19763567, compound

Product 1

HCID 23042970HCID 23042970, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 337 mg of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 1.2 g of 1-(phenylsulfonyl)-3-(2-piperazinyl)-1H-pyrrole and 5 ml of pyridine was heated in a pressure bottle at 135° C. for 16 hours, then allowed to cool and the pyridine removed under reduced pressure. The crude substance was purified by column chromatography using chloroform:methanol:water:triethylamine (9:0.5:0.01:0.01), giving 270 mg of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[3-[1-(phenylsulfonyl)-1H-pyrrol-3-yl]-1-piperazinyl]-3-quinolinecarboxylic acid.

Workup

  1. temperatureto cool
  2. customthe pyridine removed under reduced pressure
  3. customThe crude substance was purified by column chromatography

Sources & evidence

ORD record
ord-d8e8ef4745f2401bbda0c77d6faa981d
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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