Ammonium formate → N-(8-azabicyclo[3.2.1]oct-3-yl)-4-methyl-1H-indazol-5-amine

HRID 1269877Notes

Reaction equation

HRID 1269877 reaction equation
C([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]([NH:16][C:17]1[C:18]([CH3:26])=[C:19]3[C:23](=[CH:24][CH:25]=1)[NH:22][N:21]=[CH:20]3)[CH2:12]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH:9]12[NH:8][CH:13]([CH2:14][CH2:15]1)[CH2:12][CH:11]([NH:16][C:17]1[C:18]([CH3:26])=[C:19]3[C:23](=[CH:24][CH:25]=1)[NH:22][N:21]=[CH:20]3)[CH2:10]2

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18447431HCID 18447431, compound

Product 1

HCID 18447427N-(8-azabicyclo[3.2.1]oct-3-yl)-4-methyl-1H-indazol-5-amineYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the N-(8-benzyl-8-azabicyclo[3.2.1]oct-3-yl)-4-methyl-1H-indazol-5-amine (130 mg, 0.375 mmol) obtained in Example 500 in ethanol (10 ml) were added 10% Pd-C (26 mg) and then ammonium formate (118 mg, 1.87 mmol), and the resulting mixture was heated under reflux for 1 hour. The solid was removed by filtration using Celite, and the solvent was distilled off under reduced pressure. Ethyl acetate/aqueous ammonia was added to the residue, followed by extraction with ethyl acetate, 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-(8-azabicyclo[3.2.1]oct-3-yl)-4-methyl-1H-indazol-5-amine (84 mg, 88%) was obtained.

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe solid was removed by filtration
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionEthyl acetate/aqueous ammonia was added to the residue
  5. extractionfollowed by extraction with ethyl acetate
  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-227a710d19514c7a805ad16329a848d1
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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