Piperidine → HCID 68949949, compound

HRID 1453846Notes

Reaction equation

HRID 1453846 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:26]([O:28][CH3:29])=[O:27])=[N:11][N:12]2[CH:17]([CH2:18]OS(C)(=O)=O)[CH2:16][N:15]([CH3:24])[C:14](=[O:25])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1CCCCC1>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:10]([C:26]([O:28][CH3:29])=[O:27])=[N:11][N:12]2[C:17]([CH3:18])=[CH:16][N:15]([CH3:24])[C:14](=[O:25])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86617819HCID 86617819, compound

Product 1

HCID 68949949HCID 68949949, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-benzyloxy-5-methyl-7-methylsulfonyloxymethyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate (57 mg, 0.14 mmol) in anhydrous DMF under an atmosphere of nitrogen was added piperidine (133 μL, 1.35 mmol). The reaction was stirred at room temperature for 2 hours, heated to 50° C. for 2 hours, and stirred at room temperature overnight. Purification by reverse phase chromatography on a C-18 column using a gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA) and collection and concentration of the appropriate fractions afforded the title product. ES MS (M+H)=328.

Workup

  1. temperatureheated to 50° C. for 2 hours
  2. stirringstirred at room temperature overnight
  3. customPurification by reverse phase chromatography on a C-18 column
  4. washa gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA) and collection and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-9d523bd4f75d4079bfe073ee9c050f1f
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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