Water → HCID 22106211, compound

HRID 1456374Notes

Reaction equation

HRID 1456374 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]([OH:21])[CH:16]=2)=[C:7]([NH:22][C:23]([NH:25][C:26]2[C:31]([CH:32]([CH3:34])[CH3:33])=[CH:30][CH:29]=[CH:28][C:27]=2[CH:35]([CH3:37])[CH3:36])=[O:24])[C:6]1=[O:38])[CH2:2][CH2:3][CH3:4].[H-].[Na+].[C:41]([O:44][CH2:45][CH2:46]Br)(=[O:43])[CH3:42].O>CN(C=O)C>[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][CH2:46][CH2:45][O:44][C:41](=[O:43])[CH3:42])[CH:16]=2)=[C:7]([NH:22][C:23]([NH:25][C:26]2[C:27]([CH:35]([CH3:37])[CH3:36])=[CH:28][CH:29]=[CH:30][C:31]=2[CH:32]([CH3:33])[CH3:34])=[O:24])[C:6]1=[O:38])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 135641-Acetoxy-2-bromoethaneHCID 24758Sodium hydrideHCID 12972101HCID 12972101, compound

Product 1

HCID 22106211HCID 22106211, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(1-butyl-4-(3-hydroxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl)-N'-(2,6-diisopropylphenyl)urea (300 mg, 0.59 mmol) in DMF (10 ml) was added sodium hydride (NaH, 23 mg, 0.59 mmol), and the mixture was stirred at room temperature for 0.5 hour. To the mixture was added 2-bromoethyl acetate (98 mg, 0.59 mmol), and the mixture was stirred at 40°-50° C. for 6 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 anhydrous magnesium sulfate. The residue was concentrated under reduced pressure, and purified by silica gel column chromatography (3% methanol in chloroform) to give the title compound (209 mg, 0.35 mmol) as a colorless powder.

Workup

  1. stirringthe mixture was stirred at 40°-50° C. for 6 hours
  2. temperaturefor cooling
  3. extractionextracted with ethyl acetate
  4. washthe extract was washed with water
  5. washwashed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe residue was concentrated under reduced pressure
  8. custompurified by silica gel column chromatography (3% methanol in chloroform)

Sources & evidence

ORD record
ord-f871d6ebd5a848cbaf78089018acd247
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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