Water → HCID 68458196, compound

HRID 901109Notes

Reaction equation

[CH:1](Cl)(Cl)Cl.[CH2:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([F:23])=[C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH:15]=2)[C:10](=[O:24])[C:9]([C:25]([OH:27])=[O:26])=[CH:8]1)[CH3:6].C(N([CH2:33][CH3:34])CC)C.[OH2:35]>>[CH2:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([F:23])=[C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:1](=[O:35])[CH:33]=[CH2:34])[CH2:19][CH2:18]3)[CH:15]=2)[C:10](=[O:24])[C:9]([C:25]([OH:27])=[O:26])=[CH:8]1)[CH3:6]

Participants

Reactant 4

HCID 962Water

HCID 4539Norfloxacin

HCID 6212Chloroform

HCID 8471Triethylamine

Product 1

HCID 68458196HCID 68458196, compound

Procedure

Under nitrogen conditions, 30 ml of chloroform were added to 500 mg (1.567 mmol) of 1-ethyl-6-fluoro-1,4-dihydro-7-(1-piperazinyl)-4-oxo-3-quinoline carboxylic acid in a round flask of 50 ml, into which 0.436 ml (3.134 mmol) of triethylamine was then charged and stirred at room temperature for 10 minutes. While the inside temperature of the container was maintained at −10° C., 0.127 ml (1.567 mmol) of acrylochloride was slowly dripped thereinto and reacted. The reaction was conducted under nitrogen at −10° C. for 3 hours, then distilled water was added to the reactants, which were then extracted with dichloromethane. The extracts were concentrated and then chromatographed (20 gm silica, 7% MeOH/CH2Cl2) to give 1-ethyl-6-fluoro-1,4-dihydro-7-[4-(1-oxo-2-propenyl)-1-piperazinyl]4-oxo-3-quinoline carboxylic acid.

Workup

additionwas then charged
temperatureWhile the inside temperature of the container was maintained at −10° C.
customreacted
waitThe reaction was conducted under nitrogen at −10° C. for 3 hours
extractionwere then extracted with dichloromethane
concentrationThe extracts were concentrated
customchromatographed (20 gm silica, 7% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-f058e906ec3046df8180f42ec04a9089
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07361719B2

Reaction notes

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