Acetic Acid → HCID 22933775, compound

HRID 1269746Notes

Reaction equation

HRID 1269746 reaction equation
[C:1](O)(=O)C.[NH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([NH:11][C:12]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][N:18]=[CH:17]3)=[O:13])[CH2:6]1.C=O.C([BH3-])#N.[Na+].[OH-].[Na+]>CO>[CH3:1][N:5]1[CH2:10][CH2:9][CH2:8][CH:7]([NH:11][C:12]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][N:18]=[CH:17]3)=[O:13])[CH2:6]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 22934104HCID 22934104, compound

Product 1

HCID 22933775HCID 22933775, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid (0.12 ml, 2.1 mmol) was added to a suspension of the N-(3-piperidinyl)-1H-indazole-5-carboxamide (0.100 g, 0.409 mmol) obtained in Example 139 and paraformaldehyde (0.101 g, 3.34 mmol) in methanol (3 ml), and the resulting mixture was stirred for 15 minutes and then ice-cooled. Sodium cyanoborohydride (0.128 g, 2.04 mmol) was added thereto and the resulting mixture was slowly warmed up to room temperature and stirred overnight. After a 1N-aqueous sodium hydroxide solution was added thereto, the solvent was distilled off under reduced pressure and the residue was dried up and then purified by a silica gel chromatography (eluent: chloroform/methanol/30% aqueous ammonia=100/10/1). Ethyl acetate was added thereto to precipitate a solid and the resulting suspension was stirred to wash the solid. The solid was collected by filtration and dried under reduced pressure to obtain N-(1-methylpiperidin-3-yl)-1H-indazole-5-carboxamide (0.0718 g, 68%).

Workup

  1. temperatureice-cooled
  2. stirringstirred overnight
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe residue was dried up
  5. custompurified by a silica gel chromatography (eluent: chloroform/methanol/30% aqueous ammonia=100/10/1)
  6. additionEthyl acetate was added
  7. customto precipitate a solid
  8. stirringthe resulting suspension was stirred
  9. washto wash the solid
  10. filtrationThe solid was collected by filtration
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-ec7ad55e3a084b81b7508f1175cf31c6
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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