Diisopropylethylamine → 3-((2-Methoxy-3-pyridinyl)methyl)-2,5-piperazinedione

HRID 1972656Notes

Reaction equation

HRID 1972656 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:16]([O:18]CC)=O)[CH2:7][C:8]1[C:9]([O:14][CH3:15])=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:4].C(N(CC)C(C)C)(C)C>CO>[CH3:15][O:14][C:9]1[C:8]([CH2:7][CH:6]2[NH:5][C:3](=[O:4])[CH2:2][NH:1][C:16]2=[O:18])=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 66582541Ethyl glycyl-3-(2-methoxy-3-pyridinyl)alaninate

Product 1

HCID 665830063-((2-Methoxy-3-pyridinyl)methyl)-2,5-piperazinedioneYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a 100-mL round-bottomed flask was added ethyl glycyl-3-(2-methoxy-3-pyridinyl)alaninate (1.018 g, 3.62 mmol) and N,N-diisopropylethylamine (0.63 mL, 3.62 mmol) in MeOH (20 mL). The reaction mixture was stirred at 70° C. for 36 h. The solvent was partially removed under a vacuum and the solid formed was filtered, washed with MeOH and dried to give 3-((2-methoxy-3-pyridinyl)methyl)-2,5-piperazinedione (0.732 g) as a white solid.

Workup

  1. customThe solvent was partially removed under a vacuum
  2. customthe solid formed
  3. filtrationwas filtered
  4. washwashed with MeOH
  5. customdried

Sources & evidence

ORD record
ord-53081f13d7e940efbbcf9389654b6b10
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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