Ciprofloxacin → HCID 13337940, compound

HRID 1284527Notes

Reaction equation

HRID 1284527 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.[C:25]([NH2:29])(=[O:28])[CH:26]=[CH2:27]>CN(C)C=O>[C:25]([CH2:26][CH2:27][N:17]1[CH2:18][CH2:19][N:14]([C:11]2[CH:12]=[C:13]3[C:8]([C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5][N:4]3[CH:1]3[CH2:2][CH2:3]3)=[CH:9][C:10]=2[F:20])[CH2:15][CH2:16]1)(=[O:28])[NH2:29]

Participants

4

Reactant 2

HCID 2764CiprofloxacinHCID 6579Acrylamide

Product 1

HCID 13337940HCID 13337940, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3.31 g (0.01 mole) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid and 4.2 g (0.058 mole) of acrylamide in 50 ml of dimethylformamide is heated at 140° C. for 6 hours. The suspension is concentrated under a high vacuum and the residue is stirred with water and recrystallized from glycol monomethyl ether. 2 g (50% of theory) of 7-[4-(2-carbamoylethyl)-1-piperazinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid of decomposition point 283° to 286° C. are obtained.

Workup

  1. concentrationThe suspension is concentrated under a high vacuum
  2. customrecrystallized from glycol monomethyl ether

Sources & evidence

ORD record
ord-72760e9557bc4a399f869f0ea16794a3
Source dataset
uspto-grants-1986_01
Patent number
US04563448

Reaction notes

Loading…