Potassium Iodide → HCID 15483850, compound

HRID 2229392Notes

Reaction equation

HRID 2229392 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11](=[O:19])[C:10]=2[NH:20][C:21]([NH:23][C:24]2[CH:29]=[C:28]([CH2:30][N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[CH:27]=[CH:26][C:25]=2[C:37]([CH3:40])([CH3:39])[CH3:38])=[O:22])[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].I[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]>CN(C=O)C.O>[CH2:50]([N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][N:14]=2)[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[C:10]([NH:20][C:21]([NH:23][C:24]2[CH:29]=[C:28]([CH2:30][N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[CH:27]=[CH:26][C:25]=2[C:37]([CH3:40])([CH3:39])[CH3:38])=[O:22])[C:11]1=[O:19])[CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 125271-IodohexaneHCID 15483849HCID 15483849, compound

Product 1

HCID 15483850HCID 15483850, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N′-[2-tert-butyl-5-(morpholinomethyl)phenyl]urea (300 mg, 0.55 mmol) in DMF (10 ml) are added successively potassium carbonate (91.8 mg, 0.66 mmol), potassium iodide (18.4 mg, 0.11 mmol) and 1-iodohexane (117 mg, 0.55 mmol), and the mixture is stirred at room temperature for one hour, and stirred at 40-50° C. for 4 hours. The reaction solution is poured into water, and the mixture is extracted with ethyl acetate. The extract is washed with water and a saturated brine, and dried over anhydrous magnesium sulfate. The solvent is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography (chloroform→3% methanol/chloroform) to give the title compound (290 mg, 0.47 mmol) as colorless oil.

Workup

  1. stirringstirred at 40-50° C. for 4 hours
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe extract is washed with water
  4. dry with materiala saturated brine, and dried over anhydrous magnesium sulfate
  5. concentrationThe solvent is concentrated under reduced pressure
  6. customthe resulting residue is purified by silica gel column chromatography (chloroform→3% methanol/chloroform)

Sources & evidence

ORD record
ord-4eb27e7aee0b4b9495a7331581dbc91b
Source dataset
uspto-grants-2002_07
Patent number
US06420381B1

Reaction notes

Loading…