Hydrochloric Acid → HCID 178448697, compound

HRID 2229402Notes

Reaction equation

HRID 2229402 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][CH2:22][CH2:23][CH2:24][O:25]CC3C=CC=CC=3)[CH:16]=2)=[C:7]([NH:33][C:34]([NH:36][C:37]2[CH:42]=[C:41]([CH2:43][C:44]3[CH:48]=[CH:47][NH:46][N:45]=3)[CH:40]=[CH:39][C:38]=2[C:49]([CH3:52])([CH3:51])[CH3:50])=[O:35])[C:6]1=[O:53])[CH2:2][CH2:3][CH3:4].Cl>CO.[C].[Pd]>[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][CH2:22][CH2:23][CH2:24][OH:25])[CH:16]=2)=[C:7]([NH:33][C:34]([NH:36][C:37]2[CH:42]=[C:41]([CH2:43][C:44]3[CH:48]=[CH:47][NH:46][N:45]=3)[CH:40]=[CH:39][C:38]=2[C:49]([CH3:52])([CH3:51])[CH3:50])=[O:35])[C:6]1=[O:53])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178448698HCID 178448698, compound

Product 1

HCID 178448697HCID 178448697, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A suspension of N-[1-butyl-4-[3-[3-(benzyloxy)propoxy]phenyl]-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N′-[2-tert-butyl-5-(1-pyrazolylmethyl)phenyl]urea (1.86 g, 2.6 mmol), 10% palladium carbon (180 mg), conc. hydrochloric acid (0.21 ml, 2.6 mmol) in methanol is stirred under hydrogen atmosphere at room temperature for 8 hours. The mixture is filtered on celite, and the solvent is concentrated under reduced pressure. The resultant is dissolved in chloroform, and thereto are added water and aqueous ammonia. The mixture is stirred and the chloroform layer is dried over anhydrous sodium sulfate, and the solvent is concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give the title compound (1.53 g, 2.46 mmol) as colorless amorphous.

Workup

  1. filtrationThe mixture is filtered on celite
  2. concentrationthe solvent is concentrated under reduced pressure
  3. dissolutionThe resultant is dissolved in chloroform
  4. additionare added water and aqueous ammonia
  5. stirringThe mixture is stirred
  6. dry with materialthe chloroform layer is dried over anhydrous sodium sulfate
  7. concentrationthe solvent is concentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-59314a994e3048e18aab489102ba2327
Source dataset
uspto-grants-2002_07
Patent number
US06420381B1

Reaction notes

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