Sodium Iodide → 5-Fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydro-quinoline 2-carboxy-[2-(4-methylpiperazin-1-yl)ethyl]amide

HRID 2048006Notes

Reaction equation

HRID 2048006 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[F:16][C:17]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH3:30])=[C:23]2[C:18]=1[C:19](=[O:39])[C:20]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)=[CH:21][NH:22]2.[C:40]([CH:43](Cl)[CH2:44][NH-:45])([OH:42])=[O:41]>O.CN(C=O)C>[F:16][C:17]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH3:30])=[C:23]2[C:18]=1[C:19](=[O:39])[C:20]([C:31]1[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=1)=[CH:21][NH:22]2.[C:40]([CH:43]([N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)[CH2:44][NH-:45])([OH:42])=[O:41]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 86658928HCID 86658928, compound

Product 1

HCID 866589305-Fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydro-quinoline 2-carboxy-[2-(4-methylpiperazin-1-yl)ethyl]amideYield 14.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N-methylpiperazine (276 mg, 2.76 mmol), sodium iodide (440 mg, 2.9 mmol) and potassium carbonate (572 mg, 4.14 mmol) were added to a DMF solution (8 ml) of 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydroquinoline-2-carboxy-(2-chloroethyl)amide (600 mg, 1.38 mmol) and stirred overnight at 80° C. The mixture was cooled to room temperature, and water was then added thereto, followed by extraction using chloroform. The thus-obtained organic layer was concentrated under reduced pressure, and the residue was then purified using medium pressure liquid chromatography (NH silica gel, dichloromethane:methanol=100:0→10:1). The purified product was concentrated under reduced pressure, giving a white powder of 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydro-quinoline-2-carboxy-[2-(4-methylpiperazin-1-yl)ethyl]amide (100 mg, yield: 14%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionfollowed by extraction
  3. concentrationThe thus-obtained organic layer was concentrated under reduced pressure
  4. customthe residue was then purified
  5. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bfdfd7e5895841058a8e194976245b58
Source dataset
uspto-grants-2013_11
Patent number
US08592593B2

Reaction notes

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