Acetic Acid → HCID 14467953, compound

HRID 1352124Notes

Reaction equation

HRID 1352124 reaction equation
[CH2:1]1[C:6](=O)[CH2:5][CH2:4][N:3]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:2]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>[NH:22]1[C:23]2[C:19](=[CH:18][C:17]([NH:16][CH:6]3[CH2:5][CH2:4][N:3]([CH2:8][CH2:9][C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[CH2:2][CH2:1]3)=[CH:25][CH:24]=2)[CH:20]=[N:21]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 880121H-Indazol-5-amineHCID 96437N-Phenethyl-4-piperidinoneHCID 516892Sodium Bicarbonate

Product 1

HCID 14467953HCID 14467953, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(2-Phenethyl)-4-piperidone (142 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 (104 mg, yield 65%).

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-6481a33c19264b5ca5b7a227419147c5
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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