Ethyl (2E)-4-{[(4-acetyl-1H-pyrrol-2-yl)carbonyl]amino}but-2-enoate → Ethyl (7-acetyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl)acetate

HRID 2284455Notes

Reaction equation

HRID 2284455 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:9]([NH:11][CH2:12]/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:10])[NH:7][CH:8]=1)(=[O:3])[CH3:2]>C(#N)C>[C:1]([C:4]1[CH:5]=[C:6]2[C:9](=[O:10])[NH:11][CH2:12][CH:13]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:7]2[CH:8]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 86731548Ethyl (2E)-4-{[(4-acetyl-1H-pyrrol-2-yl)carbonyl]amino}but-2-enoate

Product 1

HCID 86731549Ethyl (7-acetyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl)acetateYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Diaza(1,3)bicyclo[5.4.0]undecane (DBU) (0.04 mL, 0.3 mmol) was added to a solution of ethyl (2E)-4-{[(4-acetyl-1H-pyrrol-2-yl)carbonyl]amino}but-2-enoate (0.343 g, 1.3 mmol) in acetonitrile (8 mL) and the reaction mixture was stirred at room temperature for 30 min. The solvent was evaporated under vacuum and the residue purified by flash chromatography (SiO2, hexane-EtOAc 1:1) to obtain the title compound as an off-white solid (0.24 g, 70% yield).

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe residue purified by flash chromatography (SiO2, hexane-EtOAc 1:1)

Sources & evidence

ORD record
ord-6cebb86131334929b93de1f0b7530672
Source dataset
uspto-grants-2015_09
Patent number
US09145418B2

Reaction notes

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