Acetic Acid → HCID 17838060, compound

HRID 1352175Notes

Reaction equation

HRID 1352175 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH:10]([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][N:21]=[CH:20]2.C(O)(=O)C.C(=O)([O-])O.[Na+]>CO.C(O)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][N:21]=[CH:20]3)[CH:10]([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 880121H-Indazol-5-amineHCID 516892Sodium BicarbonateHCID 5609651-Benzyl-3-methyl-4-piperidone

Product 1

HCID 17838060HCID 17838060, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

1-Benzyl-3-methyl-4-piperidone (152.7 mg), 5-aminoindazole (100 mg), and acetic acid (0.02 ml) were dissolved in methanol (10 ml). Acetic acid (five drops) was added to the solution, and a borane-pyridine complex (0.06 ml) was then added dropwise to the solution at room temperature. The reaction mixture was stirred at room temperature for 18 hr. After the completion of the reaction, a saturated aqueous sodium hydrogencarbonate solution (1 ml) was added thereto, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine and was dried over sodium sulfate. The solvent was then removed by distillation under the reduced pressure. The residue was purified by column chromatography [silica gel, chloroform/methanol] to give the title compound (95.3 mg, yield 65%).

Workup

  1. additiona borane-pyridine complex (0.06 ml) was then added dropwise to the solution at room temperature
  2. customAfter the completion of the reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water and saturated brine
  5. dry with materialwas dried over sodium sulfate
  6. customThe solvent was then removed by distillation under the reduced pressure
  7. customThe residue was purified by column chromatography [silica gel, chloroform/methanol]

Sources & evidence

ORD record
ord-4069827c00824927a7b04b156be64697
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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