Pyridine → 1-Cyclopropyl-6-fluoro-1,4-dihydro-7-[4-(2-methyl-1-oxo-2-propenyl)-1-piperazinyl]-4-oxo-3-quinoline carboxylic acid

HRID 901110Notes

Reaction equation

HRID 901110 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.N1C=CC=CC=1.[C:31](Cl)(=[O:35])[C:32]([CH3:34])=[CH2:33]>C(Cl)(Cl)Cl>[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]([C:31](=[O:35])[C:32]([CH3:34])=[CH2:33])[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

5

Reactant 3

HCID 1049PyridineHCID 2764CiprofloxacinHCID 13528Methacryloyl chloride

Product 1

HCID 595618901-Cyclopropyl-6-fluoro-1,4-dihydro-7-[4-(2-methyl-1-oxo-2-propenyl)-1-piperazinyl]-4-oxo-3-quinoline carboxylic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

700 mg (2.024 mmol) of 1-cyclopropyl-6-fluoro-1,4-dihydro-7-(1-piperazinyl)-4-oxo-3-quinoline carboxylic acid were added to a round 3-neck flask of 50 ml under a nitrogen atmosphere, and then stirred at room temperature for 10 minutes after 30 ml of chloroform and 0.491 ml (3 mmol) of pyridine were added thereto. While the temperature of the inside of the container was kept at −10° C., 0.197 ml (2.024 mmol) of methacryloylchloride was slowly dripped thereinto. After reaction for 3 hours, distilled water was added to the reactants, which were then extracted with dichloromethane, concentrated, and chromatographed (20 gm silica, 7% MeOH/CH2Cl2) to give 1-cyclopropyl-6-fluoro-1,4-dihydro-7-[4-(2-methyl-1-oxo-2-propenyl)-1-piperazinyl]-4-oxo-3-quinoline carboxylic acid.

Workup

  1. additionwere added
  2. customwas kept at −10° C.
  3. customAfter reaction for 3 hours
  4. distillationdistilled water
  5. additionwas added to the reactants, which
  6. extractionwere then extracted with dichloromethane
  7. concentrationconcentrated
  8. customchromatographed (20 gm silica, 7% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-e77f959017514197a9be402cdf5fcfc6
Source dataset
uspto-grants-2008_04
Patent number
US07361719B2

Reaction notes

Loading…