Acetic Acid → HCID 9836178, compound

HRID 1352122Notes

Reaction equation

HRID 1352122 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][N:20]=[CH:19]2.C(O)(=O)C.C(=O)([O-])O.[Na+]>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[NH:21][N:20]=[CH:19]3)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 192201-Benzyl-4-piperidoneHCID 880121H-Indazol-5-amineHCID 516892Sodium Bicarbonate

Product 1

HCID 9836178HCID 9836178, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Benzyl-4-piperidone (635 mg), 5-aminoindazole (532 mg), and acetic acid (0.20 ml) were dissolved in methanol (10 ml), and a borane-pyridine complex (0.51 ml) was added dropwise to the solution at room temperature. The reaction mixture was stirred at room temperature for 18 hr. A saturated aqueous sodium hydrogencarbonate solution (10 ml) was then added thereto, and the mixture was extracted with chloroform-propanol (3/1). The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel [chloroform/methanol] to give the title compound (1.00 g, yield 82%).

Workup

  1. additiona borane-pyridine complex (0.51 ml) was added dropwise to the solution at room temperature
  2. extractionthe mixture was extracted with chloroform-propanol (3/1)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was removed by distillation under the reduced pressure
  5. customThe residue was purified by column chromatography on silica gel [chloroform/methanol]

Sources & evidence

ORD record
ord-c53184ff2bbe4b15989fa39573541f6c
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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