Ammonium formate → HCID 86659413, compound

HRID 1187753Notes

Reaction equation

HRID 1187753 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[CH:16]=[C:15]([C:17]3[CH2:18][CH2:19][N:20]([S:23]([CH3:26])(=[O:25])=[O:24])[CH2:21][CH:22]=3)[CH:14]=[C:13]([NH:27][C:28]3[CH:33]=[N:32][CH:31]=[CH:30][N:29]=3)[N:12]=2)[CH3:9])=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>CO.[OH-].[Pd+2].[OH-]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][C:11]2[CH:16]=[C:15]([CH:17]3[CH2:18][CH2:19][N:20]([S:23]([CH3:26])(=[O:25])=[O:24])[CH2:21][CH2:22]3)[CH:14]=[C:13]([NH:27][C:28]3[CH:33]=[N:32][CH:31]=[CH:30][N:29]=3)[N:12]=2)[CH3:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 86659412HCID 86659412, compound

Product 1

HCID 86659413HCID 86659413, compoundYield 38.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 887MethanolSolvent

Procedure

88 mg of (S)—N2-[1-(4-fluorophenyl)ethyl]-4-[1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-N6-(pyrazin-2-yl)pyridine-2,6-diamine was dissolved in 5 ml of methanol, and 599 mg of ammonium formate and 18 mg of palladium hydroxide 20% on carbon were added thereto, and the mixture was heated at reflux for 3 hours. 599 mg of ammonium formate and 18 mg of palladium hydroxide 20% on carbon were added to the reaction solution, and the reaction solution was further heated at reflux for 2 hours. The reaction solution was filtrated to remove precipitates, and then the filtrate was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate. The solution was washed in turn with water and brine, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 34 mg of the objective compound as pale yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperaturethe reaction solution was further heated
  4. temperatureat reflux for 2 hours
  5. filtrationThe reaction solution was filtrated
  6. customto remove
  7. customprecipitates
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. additionThe obtained residue was diluted with ethyl acetate
  10. washThe solution was washed in turn with water and brine
  11. dry with materialdried over magnesium sulfate
  12. distillationThe solvent was distilled off under reduced pressure
  13. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-12e8e664c9754165865f860e5f2d35f8
Source dataset
uspto-grants-2014_03
Patent number
US08673891B2

Reaction notes

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