Ammonium formate → HCID 22934023, compound

HRID 1269752Notes

Reaction equation

HRID 1269752 reaction equation
C([O-])=O.[NH4+].C([N:12]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]([NH:19][C:20]([C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][N:26]=[CH:25]3)=[O:21])[CH2:13]1)C1C=CC=CC=1>C(O)C.[C].[Pd]>[NH:12]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]([NH:19][C:20]([C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][N:26]=[CH:25]3)=[O:21])[CH2:13]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22933855HCID 22933855, compound

Product 1

HCID 22934023HCID 22934023, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Ammonium formate (716 mg, 11.4 mmol) and 10% palladium carbon (containing 50% water, 100 mg) were added to a solution of the N-(1-benzylazepan-3-yl)-1H-indazole-5-carboxamide (494 mg, 1.42 mmol) obtained in Example 147 in ethanol (28 ml) at room temperature, and the resulting mixture was stirred with heating under reflux for 5 hours. The reaction mixture was filtered to remove the catalyst and the solvent of the filtrate was distilled off under reduced pressure. The resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/methanol/aqueous ammonia=10/1/0.1) to obtain N-azepan-3-yl-1H-indazole-5-carboxamide (267 mg, 73%).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 5 hours
  3. filtrationThe reaction mixture was filtered
  4. customto remove the catalyst
  5. distillationthe solvent of the filtrate was distilled off under reduced pressure
  6. customThe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/methanol/aqueous ammonia=10/1/0.1)

Sources & evidence

ORD record
ord-886f0bf40f8b41349bd130340661144a
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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