Potassium Iodide → HCID 70149984, compound

HRID 2229398Notes

Reaction equation

HRID 2229398 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[C:7]([NH:23][C:24]([NH:26][C:27]2[C:32]([CH:33]([CH3:35])[CH3:34])=[CH:31][C:30]([OH:36])=[CH:29][C:28]=2[CH:37]([CH3:39])[CH3:38])=[O:25])[C:6]1=[O:40])[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl.Cl[CH2:51][CH2:52][CH2:53][N:54]1[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]1>CN(C=O)C.O>[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[C:7]([NH:23][C:24]([NH:26][C:27]2[C:32]([CH:33]([CH3:35])[CH3:34])=[CH:31][C:30]([O:36][CH2:51][CH2:52][CH2:53][N:54]3[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]3)=[CH:29][C:28]=2[CH:37]([CH3:39])[CH3:38])=[O:25])[C:6]1=[O:40])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 79624N-(3-chloropropyl)piperidine hydrochlorideHCID 18467081HCID 18467081, compound

Product 1

HCID 70149984HCID 70149984, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of N-[1-butyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N′-(2,6-diisopropyl-4-hydroxyphenyl)urea(254 mg, 0.47 mmol) in DMF (7 ml) are added successively potassium carbonate (193 mg, 1.40 mmol), potassium iodide (39 mg, 0.23 mmol), 1-(3-chloropropyl)piperidine hydrochloride (111 mg, 0.56 mmol) at room temperature, and the mixture is stirred at about 45° C. for 5 hours. To the mixture is added water, and the mixture is extracted with ethyl acetate. The extract is washed with water and a saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (ethyl acetate:hexane=3:2→3% ethanol/ethyl acetate) to give the title compound (168 mg, 0.25 mmol) as amorphous.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe extract is washed with water
  3. dry with materiala saturated brine, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (ethyl acetate:hexane=3:2→3% ethanol/ethyl acetate)

Sources & evidence

ORD record
ord-94a16ad4dae94b948a5a584f38ca2e92
Source dataset
uspto-grants-2002_07
Patent number
US06420381B1

Reaction notes

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