Acetic Acid → HCID 17838238, compound

HRID 1352121Notes

Reaction equation

HRID 1352121 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1)[CH3:2].[NH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][N:15]=[CH:14]2.C(O)(=O)C.C(=O)([O-])O.[Na+]>CO>[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([NH:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[CH:14]3)[CH2:5][CH2:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 771591-Ethylpiperidin-4-oneHCID 880121H-Indazol-5-amineHCID 516892Sodium Bicarbonate

Product 1

HCID 17838238HCID 17838238, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Ethyl-4-piperidone (76 mg), 5-aminoindazole (67 mg), and acetic acid (0.02 ml) were dissolved in methanol (1 ml), and a borane-pyridine complex (0.06 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 (1 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 HPLC [chloroform/methanol] to give the title compound (50 mg, yield 41%).

Workup

  1. additiona borane-pyridine complex (0.06 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 HPLC [chloroform/methanol]

Sources & evidence

ORD record
ord-51fb415d59ff416c91a0069dd2859650
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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