Ammonium formate → N-(1H-indazol-5-yl)piperidine-4-sulfonamide

HRID 1269773Notes

Reaction equation

HRID 1269773 reaction equation
C([O-])=O.[NH4+].[NH:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][S:15]([CH:18]3[CH2:23][CH2:22][N:21](C(OCC4C=CC=CC=4)=O)[CH2:20][CH2:19]3)(=[O:17])=[O:16])=[CH:11][CH:12]=2)[CH:7]=[N:6]1>C(O)C.[Pd]>[NH:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][S:15]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)(=[O:17])=[O:16])=[CH:11][CH:12]=2)[CH:7]=[N:6]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18447213benzyl 4-[(1H-indazol-5-ylamino)sulfonyl]piperidine-1-carboxylate

Product 1

HCID 22933603N-(1H-indazol-5-yl)piperidine-4-sulfonamideYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ammonium formate (250 mg) and 10%-Pd/C (50 mg) were added to a solution of benzyl 4-[(1H-indazol-5-ylamino)sulfonyl]piperidine-1-carboxylate (250 mg, 0.603 mmol) in ethanol (15 ml) at room temperature, and the resulting mixture was refluxed for 1 hour. The reaction mixture was filtered by the use of Celite, and the filtrate was concentrated and the resulting residue was dissolved in a mixture of chloroform and methanol, followed by adding thereto diethyl ether. The solid precipitated was collected by filtration and dried under reduced pressure to obtain N-(1H-indazol-5-yl)piperidine-4-sulfonamide (116 mg, 69%).

Workup

  1. temperaturethe resulting mixture was refluxed for 1 hour
  2. filtrationThe reaction mixture was filtered by the use of Celite
  3. concentrationthe filtrate was concentrated
  4. dissolutionthe resulting residue was dissolved in a mixture of chloroform and methanol
  5. additionby adding
  6. customThe solid precipitated
  7. filtrationwas collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-c8e00c56e0114c83a60066a84584f961
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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