Water → HCID 15483854, compound

HRID 2229394Notes

Reaction equation

HRID 2229394 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[CH:32]=[C:31]([CH2:33]Br)[CH:30]=[CH:29][C:28]=2[C:35]([CH3:38])([CH3:37])[CH3:36])=[O:25])[C:6]1=[O:39])[CH2:2][CH2:3][CH3:4].[NH:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1.O>C1COCC1>[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[CH:32]=[C:31]([CH2:33][N:40]3[CH2:44][CH2:43][CH2:42][CH2:41]3)[CH:30]=[CH:29][C:28]=2[C:35]([CH3:38])([CH3:37])[CH3:36])=[O:25])[C:6]1=[O:39])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 31268PyrrolidineHCID 18467089HCID 18467089, compound

Product 1

HCID 15483854HCID 15483854, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[1-butyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N′-[2-tert-butyl-5-(bromomethyl)phenyl]urea (330 mg, 0.56 mmol) in THF (tetrahydrofuran, 5 ml) is added pyrrolidine (362 mg, 5.09 mmol), and the mixture is stirred at room temperature for 3 hours. The mixture 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 evaporated under reduced pressure, and the resulting residue is purified by silica gel column chromatography (5-10% methanol/chloroform) to give the title compound (234 mg, 0.42 mmol) as colorless oil.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe extract is washed with water
  3. dry with materiala saturated brine, and dried over anhydrous magnesium sulfate
  4. customThe solvent is evaporated under reduced pressure
  5. customthe resulting residue is purified by silica gel column chromatography (5-10% methanol/chloroform)

Sources & evidence

ORD record
ord-0c21d72876be485d8ceb172a6d2b7a95
Source dataset
uspto-grants-2002_07
Patent number
US06420381B1

Reaction notes

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