Ciprofloxacin → HCID 13850789, compound

HRID 1382212Notes

Reaction equation

HRID 1382212 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:20])=[C:11]([N:14]4[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1.[F:25][C:26]([F:31])([F:30])[S:27][CH2:28]Cl.C(N(CC)CC)C.[I-].[K+]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:20])=[C:11]([N:14]4[CH2:19][CH2:18][N:17]([CH2:28][S:27][C:26]([F:31])([F:30])[F:25])[CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)[CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 2764CiprofloxacinHCID 4875Potassium IodideHCID 8471TriethylamineHCID 3468030Chloromethyl trifluoromethyl sulfide

Product 1

HCID 13850789HCID 13850789, compoundYield 33.7%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3.3 g (10 mmol) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid are heated at 90° in 50 ml of dimethylformamide with 4 g (27 mmol) of trifluoromethylthiomethyl chloride, 2.1 g of triethylamine, 1.7 g of potassium iodide and 0.2 g of tetrabutylammonium iodide for 16 hours. The solution is poured into 50 ml of water and the precipitate is filtered off with suction and boiled up with methanol. 1.5 g of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-trifluoromethylthiomethyl-1-piperazinyl)-3-quinolinecarboxylic acid of melting point 247°-250° (with decomposition) are obtained.

Workup

  1. filtrationthe precipitate is filtered off with suction

Sources & evidence

ORD record
ord-dd39ef5f55064a55989d36b24fe33c2d
Source dataset
uspto-grants-1989_02
Patent number
US04806539

Reaction notes

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