Hydrochloric Acid → HCID 22106125, compound

HRID 1456391Notes

Reaction equation

HRID 1456391 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][N:24](CC3C=CC=CC=3)[CH2:25][CH3:26])[CH:16]=2)=[C:7]([NH:34][C:35]([NH:37][C:38]2[C:43]([CH:44]([CH3:46])[CH3:45])=[CH:42][CH:41]=[CH:40][C:39]=2[CH:47]([CH3:49])[CH3:48])=[O:36])[C:6]1=[O:50])[CH2:2][CH2:3][CH3:4].Cl>C(O)C.[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][NH:24][CH2:25][CH3:26])[CH:16]=2)=[C:7]([NH:34][C:35]([NH:37][C:38]2[C:43]([CH:44]([CH3:46])[CH3:45])=[CH:42][CH:41]=[CH:40][C:39]=2[CH:47]([CH3:48])[CH3:49])=[O:36])[C:6]1=[O:50])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22105981HCID 22105981, compound

Product 1

HCID 22106125HCID 22106125, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-[1-butyl-4-[3-{2-(N-benzyl-N-ethylamino)ethoxy)-phenyl]-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea (129 mg, 0.191 mmol) in ethanol (10 ml) were added 12N aqueous hydrochloric acid solution (1 ml) and 10% palladium-carbon (210 mg), and the mixture was stirred at room temperature under hydrogen atmosphere for five hours. The mixture was filtered through a cerite pad, and the filtrate was concentrated. To the concentrated resultant was added aqueous ammonia, and the mixture was extracted with ethyl acetate. The extract was washed with water, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The reside was concentrated under reduced pressure, and the residue was purified by thin layer chromatography (10% methanol in chloroform) to give the title compound (63 mg, 0.10 mmol).

Workup

  1. filtrationThe mixture was filtered through a cerite pad
  2. concentrationthe filtrate was concentrated
  3. concentrationTo the concentrated resultant
  4. additionwas added aqueous ammonia
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. washwashed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationThe reside was concentrated under reduced pressure
  10. customthe residue was purified by thin layer chromatography (10% methanol in chloroform)

Sources & evidence

ORD record
ord-bc9f6c2695e8477e96c5419cd58506cb
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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