Ammonium formate → HCID 22105965, compound

HRID 1456378Notes

Reaction equation

HRID 1456378 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[C:42]([CH:43]([CH3:45])[CH3:44])=[CH:41][CH:40]=[CH:39][C:38]=2[CH:46]([CH3:48])[CH3:47])=[O:35])[C:6]1=[O:49])[CH2:2][CH2:3][CH3:4].C([O-])=O.[NH4+]>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[C:38]([CH:46]([CH3:47])[CH3:48])=[CH:39][CH:40]=[CH:41][C:42]=2[CH:43]([CH3:45])[CH3:44])=[O:35])[C:6]1=[O:49])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22106270HCID 22106270, compound

Product 1

HCID 22105965HCID 22105965, compoundYield 31.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-[1-butyl-4-{3-(3-benzyloxypropoxy)phenyl}-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea (316 mg, 0.48 mmol) in methanol (20 ml) were added ammonium formate (91 mg, 1.44 mmol) and 10% palladium-carbon (100 mg), and the mixture was refluxed for 10 hours. After allowed to stand for cooling, the mixture was filtered through a cerite pad, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the mixture was washed with water, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The residue was concentrated under reduced pressure, purified by silica gel column chromatography (1-3% methanol in chloroform), and crystallized from ether/hexane to give the title compound (85 mg, 0.15 mmol).

Workup

  1. temperaturethe mixture was refluxed for 10 hours
  2. temperaturefor cooling
  3. filtrationthe mixture was filtered through a cerite pad
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washthe mixture was washed with water
  7. washwashed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationThe residue was concentrated under reduced pressure
  10. custompurified by silica gel column chromatography (1-3% methanol in chloroform)
  11. customcrystallized from ether/hexane

Sources & evidence

ORD record
ord-c0c46e71ebfd47f898bd056cd121923d
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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