Ethyl (7-acetyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl)acetate → Ethyl {7-[(2E)-3-(dimethylamino)prop-2-enoyl]-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl}acetate

HRID 2284456Notes

Reaction equation

HRID 2284456 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[NH:10][CH2:9][CH:8]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:7]2[CH:19]=1)(=[O:3])[CH3:2]>C(OC(OC(C)(C)C)N(C)C)(C)(C)C>[CH3:6][N:7]([CH3:19])/[CH:8]=[CH:2]/[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[NH:10][CH2:9][CH:8]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:7]2[CH:19]=1)=[O:3]

Participants

3

Reactant 1

HCID 86731549Ethyl (7-acetyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl)acetate

Product 1

HCID 86731550Ethyl {7-[(2E)-3-(dimethylamino)prop-2-enoyl]-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl}acetate

Reagents, catalysts & solvents 1

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineSolvent

Conditions

Temperature
110 °C

Procedure

The intermediate ethyl (7-acetyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl)acetate 1 g (3.78 mmol) was dissolved in 5 ml of N,N-dimethylformamide ditert butyl acetal and stirred at 110° C. for 6 hours. The reaction mixture was concentrated and then partitioned between H2O and DCM. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the title compound in quantitative yield.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between H2O and DCM
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cdce99576d51403e948ad23d991d7e8c
Source dataset
uspto-grants-2015_09
Patent number
US09145418B2

Reaction notes

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