Fluoroquinolonic acid → HCID 178524693, compound

HRID 2165697Notes

Reaction equation

HRID 2165697 reaction equation
Cl[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].[NH:20]1[CH:24]=[CH:23][C:22]([CH:25]2[CH2:30][NH:29][CH2:28][CH2:27][NH:26]2)=[N:21]1>N1C=CC=CC=1>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([N:29]4[CH2:28][CH2:27][NH:26][CH:25]([C:22]5[CH:23]=[CH:24][NH:20][N:21]=5)[CH2:30]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 178419966HCID 178419966, compound

Product 1

HCID 178524693HCID 178524693, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 703 mg of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 1.14 g of 2-(1H-pyrazol-3-yl)piperazine and 5 ml of pyridine was heated in a pressure bottle at 130° C. for 24 hours. It was allowed to cool at room temperature, then cooled to 0° C., the pyridine removed and the crude product purified by flash chromatography on silica gel, giving 195 mg of the desired product.

Workup

  1. temperatureto cool at room temperature
  2. temperaturecooled to 0° C.
  3. customthe pyridine removed
  4. customthe crude product purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-59cbba88f44a4b48a68473f86d43aebe
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

Loading…