Acetic Acid → HCID 67132308, compound

HRID 1352126Notes

Reaction equation

HRID 1352126 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10](=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][N:19]=[CH:18]2.C(O)(=O)C.C(=O)([O-])O.[Na+]>CO>[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[NH:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][N:19]=[CH:18]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 698901-Benzyl-3-pyrrolidinoneHCID 880121H-Indazol-5-amineHCID 516892Sodium Bicarbonate

Product 1

HCID 67132308HCID 67132308, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Benzyl-3-pyrrolidinone (105 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 (49 mg, yield 34%).

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-99bf01f3b82a4f408b09e780a5b01676
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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