Ammonium formate → HCID 18447382, compound

HRID 1269891Notes

Reaction equation

HRID 1269891 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH:22][C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[NH:28][N:27]=[CH:26]3)=[O:15])[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[N:11]1([C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH:22][C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[NH:28][N:27]=[CH:26]3)=[O:15])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18447367HCID 18447367, compound

Product 1

HCID 18447382HCID 18447382, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the N-{2-[(4-benzylpiperazin-1-yl)carbonyl]phenyl}-1H-indazol-5-amine (127 mg, 0.309 mmol) obtained in Example 515 in ethanol (5 ml) were added 10% Pd-C (20 mg) and ammonium formate (98 mg, 1.55 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. The residue was extracted with ethyl acetate, and the extract solution was washed with a saturated aqueous sodium hydrogencarbonate solution and then a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent, whereby N-[2-(piperazin-1-ylcarbonyl)phenyl]-1H-indazol-5-amine (56 mg, 57%) was obtained.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customThe solid was removed by filtration
  4. distillationthe solvent was distilled off under reduced pressure
  5. extractionThe residue was extracted with ethyl acetate
  6. washthe extract solution was washed with a saturated aqueous sodium hydrogencarbonate solution
  7. dry with materiala saturated aqueous sodium chloride solution, dried over sodium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent

Sources & evidence

ORD record
ord-24073a779fb74aa1af56dda13a5722aa
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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