Ethylenediamine → HCID 58406323, compound

HRID 1753121Notes

Reaction equation

HRID 1753121 reaction equation
O=[C:2]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH2:3][N:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]([O:11]C)=O.[CH2:19]([NH2:22])[CH2:20][NH2:21]>O1CCOCC1>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:2]23[NH:22][CH2:19][CH2:20][N:21]2[C:9](=[O:11])[C:5]2[N:4]([CH:8]=[CH:7][CH:6]=2)[CH2:3]3)[CH:14]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 67367235HCID 67367235, compound

Product 1

HCID 58406323HCID 58406323, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 1-[2-oxo-2-(pyridin-3-yl)ethyl]-1H-pyrrole-2-carboxylate (84 mg, 0.34 mmol) in 1,4-dioxane (15 mL) was added ethane-1,2-diamine (0.65 mL, 9.7 mmol). The solution was heated at reflux for 3 days. The mixture was then concentrated in vacuo to give an oily solid. The material was purified by flash chromatography (Silica gel, gradient 5-9% methanol in CH2Cl2) to yield 10a-(pyridin-3-yl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (102) as an off-white solid (75 mg, yield 86%).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 3 days
  3. concentrationThe mixture was then concentrated in vacuo
  4. customto give an oily solid
  5. customThe material was purified by flash chromatography (Silica gel, gradient 5-9% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-7d609802c2d5479db8c50266de9542df
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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