Ammonium formate → HCID 22106111, compound

HRID 1456393Notes

Reaction equation

HRID 1456393 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]([C:21]#[C:22][CH2:23][OH:24])[CH:16]=2)=[C:7]([NH:25][C:26]([NH:28][C:29]2[C:34]([CH:35]([CH3:37])[CH3:36])=[CH:33][CH:32]=[CH:31][C:30]=2[CH:38]([CH3:40])[CH3:39])=[O:27])[C:6]1=[O:41])[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]([CH2:21][CH2:22][CH2:23][OH:24])[CH:16]=2)=[C:7]([NH:25][C:26]([NH:28][C:29]2[C:30]([CH:38]([CH3:39])[CH3:40])=[CH:31][CH:32]=[CH:33][C:34]=2[CH:35]([CH3:37])[CH3:36])=[O:27])[C:6]1=[O:41])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22105947HCID 22105947, compound

Product 1

HCID 22106111HCID 22106111, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-[1-butyl-4-{3-(3-hydroxy-1-propynyl)phenyl}-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea (10 mg, 0.02 mmol) in methanol (3 ml) were added ammonium formate (5 mg, 0.08 mmol) and 10% palladium-carbon (5 mg), and the mixture was heated under reflux for five hours. After allowed to stand for cooling, the mixture was filtered through a cerite pad, and the filtrate was concentrated. The concentrated residue was diluted with ethyl acetate, and washed with water, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The residue was concentrated under reduced pressure, and further purified by thin layer chromatography (hexane:ethyl acetate=5:5) to give the title compound (6 mg, 0.02 mmol).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for five hours
  3. temperaturefor cooling
  4. filtrationthe mixture was filtered through a cerite pad
  5. concentrationthe filtrate was concentrated
  6. additionThe concentrated residue was diluted with ethyl acetate
  7. washwashed with water
  8. washwashed with a saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationThe residue was concentrated under reduced pressure
  11. customfurther purified by thin layer chromatography (hexane:ethyl acetate=5:5)

Sources & evidence

ORD record
ord-a234708653f9402ea48443cbf3f5141b
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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