Norfloxacin → HCID 86600171, compound

HRID 901108Notes

Reaction equation

HRID 901108 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:19])=[C:10]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:20])[C:5]([C:21]([OH:23])=[O:22])=[CH:4]1)[CH3:2].[S:24]([C:32]1[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=1)([O:27][CH2:28][CH:29]1[O:31][CH2:30]1)(=[O:26])=[O:25]>CN(C)C=O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:19])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:30][CH:29]([OH:31])[CH2:28][O:27][S:24]([C:32]4[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=4)(=[O:26])=[O:25])[CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:20])[C:5]([C:21]([OH:23])=[O:22])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 4539NorfloxacinHCID 160868Glycidyl tosylate

Product 1

HCID 86600171HCID 86600171, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

39.4 mg of 1-ethyl-6-fluoro-1,4-dihydro-7-(1-piperazinyl)-4-oxo-3-quinoline carboxylic acid were mixed with 50 ml of N,N-dimethylformamide in a round flask of 100 ml and slowly stirred at room temperature for 20 minutes. 14.4 mg of glycidyl tosylate were added thereto, it was stirred at room temperature, and then washed with 30.0 ml of N,N-dimethylformamide. The reactants were held at 80° C. for 5 hours and then stirred at 25° C. for 10 minutes. The reactants were crystalized through column chromatography (20 gm silica, 10% ethylacetate/hexane), filtered, and then dried to give 11.2 mg of 1-ethyl-6-fluoro-1,4-dihydro-7-{4-[2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl]-1-piperazinyl}-4-oxo-3-quinoline carboxylic acid.

Workup

  1. stirringit was stirred at room temperature
  2. washwashed with 30.0 ml of N,N-dimethylformamide
  3. waitThe reactants were held at 80° C. for 5 hours
  4. stirringstirred at 25° C. for 10 minutes
  5. customThe reactants were crystalized through column chromatography (20 gm silica, 10% ethylacetate/hexane)
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-20df6f7913aa4393af562e29f70ea714
Source dataset
uspto-grants-2008_04
Patent number
US07361719B2

Reaction notes

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