Norfloxacin → HCID 86600171, compound

HRID 503718Notes

Reaction equation

HRID 503718 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 crystallized 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-pip erazinyl}-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 crystallized through column chromatography (20 gm silica, 10% ethylacetate/hexane)
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-8a94d6f54d9c4a63bd1c404be3f4c2a7
Source dataset
uspto-grants-2010_08
Patent number
US07777033B2

Reaction notes

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