Ammonium formate → HCID 22106239, compound

HRID 1456372Notes

Reaction equation

HRID 1456372 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2Cl)=[C:4]([NH:19][C:20]([NH:22][C:23]2[C:28]([CH:29]([CH3:31])[CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=2[CH:32]([CH3:34])[CH3:33])=[O:21])[C:3]1=[O:35].C([O-])=O.[NH4+]>CO.[C].[Pd]>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[C:5]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:4]([NH:19][C:20]([NH:22][C:23]2[C:28]([CH:29]([CH3:30])[CH3:31])=[CH:27][CH:26]=[CH:25][C:24]=2[CH:32]([CH3:34])[CH3:33])=[O:21])[C:3]1=[O:35]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 9848374HCID 9848374, compound

Product 1

HCID 22106239HCID 22106239, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-[1-methyl-4-(2-chlorophenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea (350 mg, 0.72 mmol) in methanol (20 ml) were added ammonium formate (135 mg, 2.15 mmol) and 10% palladium-carbon (100 mg), and the mixture was refluxed for 4 hours. After allowed to stand for cooling, the mixture was filtered through a cerite pad, and the filtrate was concentrated under reduced pressure. To the residue was added dilute aqueous ammonia, and the mixture was extracted with ethyl acetate. The extract was washed with water, washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and crystallized from diethyl ether to give the title compound (249 mg, mmol) as a colorless powder.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. temperaturefor cooling
  3. filtrationthe mixture was filtered through a cerite pad
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionTo the residue was added dilute aqueous ammonia
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with water
  8. washwashed with a saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-70645330abda46289cdcbb8cc3b2d569
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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