Fluoroquinolonic acid → HCID 70436198, compound

HRID 2165699Notes

Reaction equation

HRID 2165699 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].[CH:20]1([CH:23]2[CH2:28][NH:27][CH2:26][CH2:25][NH:24]2)[CH2:22][CH2:21]1>N1C=CC=CC=1>[ClH:1].[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([N:27]4[CH2:26][CH2:25][NH:24][CH:23]([CH:20]5[CH2:22][CH2:21]5)[CH2:28]4)[CH:11]=3)[C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8]2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 483180Fluoroquinolonic acidHCID 197635402-Cyclopropylpiperazine

Product 1

HCID 70436198HCID 70436198, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 1.405 g of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 4.34 g of 2-cyclopropylpiperazine and 15 ml of pyridine was heated in a pressure bottle at 135° C. for 24 hours, then cooled and the pyridine removed under reduced pressure. The residue was purified by chromatography on silica gel, with chloroform:methanol:water:triethylamine (9.5:0.5:0.01:0.01). The solid (base form) was redissolved in ethanol, a few drops of concentrated hydrochloric acid were added and the solid collected, washed with cold ethanol, ether and dried, giving the desired products.

Workup

  1. temperaturecooled
  2. customthe pyridine removed under reduced pressure
  3. customThe residue was purified by chromatography on silica gel, with chloroform:methanol:water:triethylamine (9.5:0.5:0.01:0.01)
  4. dissolutionThe solid (base form) was redissolved in ethanol
  5. additiona few drops of concentrated hydrochloric acid were added
  6. customthe solid collected
  7. washwashed with cold ethanol, ether
  8. customdried

Sources & evidence

ORD record
ord-cb10f4a2e001400b9087c09b6feb82df
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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