Water → HCID 22106440, compound

HRID 1456381Notes

Reaction equation

HRID 1456381 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[C:29]([CH:30]([CH3:32])[CH3:31])=[CH:28][CH:27]=[CH:26][C:25]=2[CH:33]([CH3:35])[CH3:34])=[O:22])[CH:6]=[CH:7][CH:8]=1.Br[CH2:37][CH2:38][CH2:39][N:40]1[C:44](=[O:45])[C:43]2=[CH:46][CH:47]=[CH:48][CH:49]=[C:42]2[C:41]1=[O:50].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:41]1(=[O:50])[N:40]([CH2:39][CH2:38][CH2:37][N:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][N:14]=3)[C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)=[C:10]([NH:20][C:21]([NH:23][C:24]3[C:29]([CH:30]([CH3:31])[CH3:32])=[CH:28][CH:27]=[CH:26][C:25]=3[CH:33]([CH3:35])[CH3:34])=[O:22])[C:11]2=[O:19])[C:44](=[O:45])[C:43]2=[CH:46][CH:47]=[CH:48][CH:49]=[C:42]12

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 22106214HCID 22106214, compound

Product 1

HCID 22106440HCID 22106440, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea (200 mg, 0.43 mmol) and N-(3-bromopropyl)phthalimide (133 mg, 0.50 mmol) in DMF (10 ml) was added potassium carbonate (114 mg, 0.83 mmol), and the mixture was stirred at 50°-60° C. for one hour. After allowed to stand for cooling, the mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The residue was concentrated under reduced pressure, purified by silica gel column chromatography (1-3% methanol in chloroform), and crystallized from hexane to give the title compound (229 mg, 0.35 mmol).

Workup

  1. temperaturefor cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe residue was concentrated under reduced pressure
  7. custompurified by silica gel column chromatography (1-3% methanol in chloroform)
  8. customcrystallized from hexane

Sources & evidence

ORD record
ord-f5f8ccf0b51141f79cc8b5875342127f
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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