p-Toluenesulfonic acid → HCID 15483853, compound

HRID 2229393Notes

Reaction equation

HRID 2229393 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][O:34]C3CCCCO3)[CH:30]=[CH:29][C:28]=2[C:41]([CH3:44])([CH3:43])[CH3:42])=[O:25])[C:6]1=[O:45])[CH2:2][CH2:3][CH3:4].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[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][OH:34])[CH:30]=[CH:29][C:28]=2[C:41]([CH3:44])([CH3:43])[CH3:42])=[O:25])[C:6]1=[O:45])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 15483852HCID 15483852, compound

Product 1

HCID 15483853HCID 15483853, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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-[(tetrahydro-2H-pyran-2-yl)-oxymethyl]phenyl]urea (34.05 g, 55.6 mmol) in methanol (340 ml) is added p-toluenesulfonic acid (10.57 g, 55.6 mmol), and the mixture is stirred at room temperature for two hours. Methanol is evaporated under reduced pressure, and to the resultant is added water, and the mixture is extracted with ethyl acetate. The extract is washed with water, an aqueous sodium hydrogen carbonate solution and a saturated brine, and dried over magnesium sulfate. The solvent is evaporated under reduced pressure, and the resulting residue is purified by silica gel column chromatography (ethyl acetate:hexane=1:1→ethyl acetate:hexane=3:1) to give the title compound (21.6 g, 40.8 mmol). Some of the title compound (2.03 g) is dissolved in ethyl acetate (2 ml), and thereto is added hexane. The mixture is stirred at room temperature for 3 hours, and stirred under ice-cooling for one hour. The precipitated crystals are collected by filtration to give the title compound (1.70 g) as colorless crystals.

Workup

  1. customMethanol is evaporated under reduced pressure
  2. additionto the resultant is added water
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe extract is washed with water
  5. dry with materialan aqueous sodium hydrogen carbonate solution and a saturated brine, and dried over magnesium sulfate
  6. customThe solvent is evaporated under reduced pressure
  7. customthe resulting residue is purified by silica gel column chromatography (ethyl acetate:hexane=1:1→ethyl acetate:hexane=3:1)

Sources & evidence

ORD record
ord-11dcdec5872146c0810305df725848ec
Source dataset
uspto-grants-2002_07
Patent number
US06420381B1

Reaction notes

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