Diisopropylethylamine → 3-((2-Methoxy-4-pyridinyl)methyl)-2,5-piperazinedione

HRID 1972672Notes

Reaction equation

HRID 1972672 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:16]([O:18]CC)=O)[CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH3:15])[CH:9]=1)=[O:4].C(N(CC)C(C)C)(C)C>CO>[CH3:15][O:14][C:10]1[CH:9]=[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][N:11]=1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 66582801HCID 66582801, compound

Product 1

HCID 665829993-((2-Methoxy-4-pyridinyl)methyl)-2,5-piperazinedioneYield 93.1%

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-4-pyridinyl)alaninate (1.70 g, 6.03 mmol) and N,N-diisopropylethylamine (1.05 mL, 6.03 mmol) in MeOH (20 mL). The reaction mixture was stirred at 70° C. for 18 h and allowed to cool to room temperature. The solid formed was filtered and washed with MeOH to give 3-((2-methoxy-4-pyridinyl)methyl)-2,5-piperazinedione (1.32 g) as a white solid.

Workup

  1. temperatureto cool to room temperature
  2. customThe solid formed
  3. filtrationwas filtered
  4. washwashed with MeOH

Sources & evidence

ORD record
ord-00be31d673e0444dab498ea0afaa28a9
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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