1H-Indazol-5-amine → HCID 17838098, compound

HRID 1352139Notes

Reaction equation

HRID 1352139 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[NH2:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][N:18]=[CH:17]2.C(=O)([O-])O.[Na+]>CO>[NH:19]1[C:20]2[C:16](=[CH:15][C:14]([NH:13][CH:2]3[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]3[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:22][CH:21]=2)[CH:17]=[N:18]1

Participants

5

Reactant 3

HCID 880121H-Indazol-5-amineHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 17838098HCID 17838098, compoundYield 105.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-oxocyclohexanecarboxylate (0.85 g) and 5-aminoindazole (0.60 g) were dissolved in methanol (10 ml), and a borane-pyridine complex (0.81 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 chromatography on silica gel [chloroform/methanol] to give the title compound (1.37 g) as substantially 1:1 enantiomers.

Workup

  1. additiona borane-pyridine complex (0.81 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 chromatography on silica gel [chloroform/methanol]

Sources & evidence

ORD record
ord-bd2fc0a8294f4cdeb58f89d7ff5e67ca
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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