Ammonium formate → HCID 22934104, compound

HRID 1269745Notes

Reaction equation

HRID 1269745 reaction equation
C([O-])=O.[NH4+].C([N:12]1[CH2:17][CH2:16][CH2:15][CH:14]([NH:18][C:19]([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[NH:26][N:25]=[CH:24]3)=[O:20])[CH2:13]1)C1C=CC=CC=1>C(O)C.C(OCC)(=O)C.[Pd]>[NH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([NH:18][C:19]([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[NH:26][N:25]=[CH:24]3)=[O:20])[CH2:13]1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 22933463HCID 22933463, compound

Product 1

HCID 22934104HCID 22934104, compoundYield 96.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ammonium formate (0.363 g) and 10% Pd—C (0.074 g) were added to a suspension of the N-(1-benzylpiperidin-3-yl)-1H-indazole-5-carboxamide (0.357 g, 1.06 mmol) obtained in Example 138 in ethanol (10 ml), and the resulting mixture was stirred for 4 hours with heating under reflux. The resulting solution was filtered by the use of Celite and then the solvent was distilled off from the filtrate to obtain a solid. The solid obtained was suspended in ethyl acetate, stirred to be washed, collected by filtration and dried under reduced pressure to obtain N-(3-piperidinyl)-1H-indazole-5-carboxamide (0.250 g, 96%).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. filtrationThe resulting solution was filtered by the use of Celite
  4. distillationthe solvent was distilled off from the filtrate
  5. customto obtain a solid
  6. customThe solid obtained
  7. stirringstirred
  8. washto be washed
  9. filtrationcollected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-6720f5a9c2094c5a84f94a9fd89d7237
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

Loading…