Water → HCID 18467093, compound

HRID 2229399Notes

Reaction equation

HRID 2229399 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[C:32]([CH:33]([CH3:35])[CH3:34])=[CH:31][C:30]([CH2:36][O:37][Si](C(C)(C)C)(C)C)=[CH:29][C:28]=2[CH:45]([CH3:47])[CH3:46])=[O:25])[C:6]1=[O:48])[CH2:2][CH2:3][CH3:4].O>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[C:28]([CH:45]([CH3:46])[CH3:47])=[CH:29][C:30]([CH2:36][OH:37])=[CH:31][C:32]=2[CH:33]([CH3:35])[CH3:34])=[O:25])[C:6]1=[O:48])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 962WaterHCID 18467086HCID 18467086, compound

Product 1

HCID 18467093HCID 18467093, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-[1-butyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N′-[2,6-diisopropyl-4-(tert-butyldimethylsilyloxymethyl)phenyl]urea (6.75 g, 10.1 mmol) in methanol containing 15% HCl (100 ml) is stirred at room temperature for 3 hours. Water is added to the reaction solution, and the mixture is extracted with ethyl acetate. The organic layer is washed with water (once) and an aqueous sodium hydrogen carbonate solution (once). The solvent is concentrated under reduced pressure, and the residue is purified by silica gel chromatography to give the title compound (5.0 g, 8.99 mmol) as colorless amorphous.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic layer is washed with water (once) and an aqueous sodium hydrogen carbonate solution (once)
  3. concentrationThe solvent is concentrated under reduced pressure
  4. customthe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-ecd6b2fcd2cb4dc7a32f6092b1096496
Source dataset
uspto-grants-2002_07
Patent number
US06420381B1

Reaction notes

Loading…