HCID 178499149, compound → Methyl 7-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylate

HRID 1808349Notes

Reaction equation

HRID 1808349 reaction equation
[CH2:1]([N:8]([CH2:12][C:13]1[N:14]=[CH:15][NH:16][C:17]=1[C:18]([O:20][CH3:21])=[O:19])[CH2:9][CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(#N)C>[CH2:1]([N:8]1[CH2:9][CH2:10][N:14]2[CH:15]=[N:16][C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:13]2[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 178499149HCID 178499149, compound

Product 1

HCID 57635262Methyl 7-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

TEA (28.66 mmol, 4 equiv.) was added at 0° C. to a solution of methyl 4-((benzyl(2-chloroethyl)amino)methyl)-1H-imidazole-5-carboxylate (7.16 mmol, 1 equiv.) in acetonitrile (50 ml). The resulting mixture was heated for 16 h at 80° C. It was then cooled and filtered, and the filtrate was concentrated in vacuo. The crude product was taken up in DCM and sat. sodium hydrogen carbonate solution, and the organic phase was dried and concentrated in vacuo. The resulting crude product was purified by column chromatography (silica gel, 5% MeOH in DCM), and the desired product was thus obtained in the form of a brown solid. Yield: 64%

Workup

  1. temperatureIt was then cooled
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. dry with materialsat. sodium hydrogen carbonate solution, and the organic phase was dried
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude product was purified by column chromatography (silica gel, 5% MeOH in DCM)

Sources & evidence

ORD record
ord-4a6b0c6c89a340e8846055e876062f55
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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