Hydrochloric Acid → HCID 44816722, compound

HRID 1969435Notes

Reaction equation

HRID 1969435 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:25])[C:5]([C:20]([O:22]CC)=[O:21])=[CH:6][N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][C:27]1=[O:31].OC1C=CC=C2C=1N=CC=C2.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>CN(C=O)C.CS(C)=O.[Cu]I>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:25])[C:5]([C:20]([OH:22])=[O:21])=[CH:6][N:7]2[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([N:26]2[CH2:30][CH2:29][CH2:28][C:27]2=[O:31])=[CH:17][CH:18]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 120252-PyrrolidoneHCID 14798Sodium HydroxideHCID 58297066HCID 58297066, compound

Product 1

HCID 44816722HCID 44816722, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 5-fluoro-1-(4-iodobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (0.060 g, 0.13 mmol), pyrrolidine-2-one (0.034 g, 0.40 mmol), 8-hydroxyquinoline (1.9 mg, 0.013 mmol) and potassium carbonate (0.037 g, 0.27 mmol) in 2 mL of DMF under nitrogen was added copper(I)iodide (10 mol %). The reaction mixture was heated to 100° C. for 22 hours, then cooled to room temperature. To the mixture was added 1 N NaOH (0.30 mL, 0.30 mmol). After 2 hours, the mixture was acidified with 6 N HCl to pH ˜2, diluted with DMSO (2 mL), filtered, and purified via reverse phase HPLC to provide the title compound which gave a proton NMR spectrum consistent with theory and a mass ion (ES+) of 381.1 for M+H+: 1H NMR (400 MHz, d6-DMSO) δ 9.25 (s, 1H), 7.86-7.80 (m, 1H), 7.66-7.64 (m, 3H), 7.36 (dd, J=8.1 Hz, 3.4 Hz, 1H), 7.30 (d, J=8.7 Hz, 2H), 5.81 (s, 2H), 3.78 (t, J=7.1 Hz, 2H), 2.51-2.44 (m, 2H), 2.07-2.01 (m, 2H).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-26d09467ccb1423db081f2170ead2b3f
Source dataset
uspto-grants-2013_04
Patent number
US08426598B2

Reaction notes

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