Ammonium formate → N-piperidin-3-yl-1H-indazol-5-amine

HRID 1269897Notes

Reaction equation

HRID 1269897 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[CH:18]3)[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[CH:18]3)[CH2:9]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 9857714N-(1-benzylpiperidin-3-yl)-1H-indazol-5-amine

Product 1

HCID 22933426N-piperidin-3-yl-1H-indazol-5-amineYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the N-(1-benzylpiperidin-3-yl)-1H-indazol-5-amine (463 mg, 1.51 mmol) obtained in Example 535 in ethanol (10 ml) were added 10% Pd—C (50 mg) and then ammonium formate (952 mg, 15.1 mmol), and the resulting mixture was heated under reflux for 2 hours. The solid was removed by filtration using Celite, and the solvent was distilled off under reduced pressure. Chloroform/aqueous ammonia was added to the residue, followed by extraction with chloroform, and the extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent, whereby N-piperidin-3-yl-1H-indazol-5-amine (241 mg, 74%) was obtained.

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe solid was removed by filtration
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionChloroform/aqueous ammonia was added to the residue
  5. extractionfollowed by extraction with chloroform
  6. washthe extract solution was washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent

Sources & evidence

ORD record
ord-faa6a980f3ec43b0b4e196a82dc98515
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

Loading…