Ammonium formate → HCID 16727150, compound

HRID 1511827Notes

Reaction equation

HRID 1511827 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[C:11]([N:25]=1)=[N:12][C:13]([CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[CH:14][N:15]=2)=[O:5])[CH3:2].C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[C:11]([N:25]=1)=[N:12][C:13]([CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=1)=[CH:14][N:15]=2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69508459HCID 69508459, compound

Product 1

HCID 16727150HCID 16727150, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

108 mg of 1-ethyl-3-{3-[2-(4-fluorophenyl)vinyl]pyrido[2,3-b]pyrazin-6-yl}urea (0.32 mmol) (Example 27) were dissolved in hot ethanol. 112 mg of ammonium formate (1.78 mmol) and 110 mg of palladium (10%) on carbon were added, and the reaction mixture was heated under reflux for 7.5 h. The catalyst was filtered off from the cooled reaction mixture, and the mother liquor was freed from the solvent. The crude product was purified by column chromatography on silica gel (dichloromethane/methanol eluent). This gave a yellow solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 7.5 h
  3. filtrationThe catalyst was filtered off from the cooled reaction mixture
  4. customThe crude product was purified by column chromatography on silica gel (dichloromethane/methanol eluent)
  5. customThis gave a yellow solid

Sources & evidence

ORD record
ord-694d7048ccb94bae9621300c36609b6d
Source dataset
uspto-grants-2012_07
Patent number
US08217042B2

Reaction notes

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