Imidazole → HCID 22106242, compound

HRID 1456380Notes

Reaction equation

HRID 1456380 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH2:14]([N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][N:26]=2)[C:21]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH2:35][CH2:36][CH2:37]Cl)[CH:29]=2)=[C:20]([NH:39][C:40]([NH:42][C:43]2[C:48]([CH:49]([CH3:51])[CH3:50])=[CH:47][CH:46]=[CH:45][C:44]=2[CH:52]([CH3:54])[CH3:53])=[O:41])[C:19]1=[O:55])[CH2:15][CH2:16][CH3:17]>CN(C=O)C.O>[CH2:14]([N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][N:26]=2)[C:21]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH2:35][CH2:36][CH2:37][N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)[CH:29]=2)=[C:20]([NH:39][C:40]([NH:42][C:43]2[C:48]([CH:49]([CH3:51])[CH3:50])=[CH:47][CH:46]=[CH:45][C:44]=2[CH:52]([CH3:53])[CH3:54])=[O:41])[C:19]1=[O:55])[CH2:15][CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 22105972HCID 22105972, compound

Product 1

HCID 22106242HCID 22106242, compoundYield 38.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of imidazole (97 mg, 1.43 mmol), potassium carbonate (246 mg, 1.78 mmol) and sodium iodide (35 mg) in DMF (20 ml) was added N-[1-(butyl-4-{3-(3-chloropropoxy)phenyl}-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea (700 mg, 1.19 mmol), and the mixture was stirred at 50°-60° C. for 10 hours. After allowed to stand for cooling, the mixture was poured into water, extracted with ethyl acetate, and the extract was washed with water, washed with a saturated aqueous sodium chloride solution, and dried over magnesium sulfate. The residue was concentrated under reduced pressure, and purified by silica gel column chromatography (5% methanol in chloroform) to give the title compound (286 mg, 0.46 mmol).

Workup

  1. temperaturefor cooling
  2. extractionextracted with ethyl acetate
  3. washthe extract was washed with water
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe residue was concentrated under reduced pressure
  7. custompurified by silica gel column chromatography (5% methanol in chloroform)

Sources & evidence

ORD record
ord-fa3c43564139407295add8faec42c623
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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