Ethylenediamine → HCID 67368936, compound

HRID 1753184Notes

Reaction equation

HRID 1753184 reaction equation
O=[C:2]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=1)[CH2:3][N:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]([O:11]C)=O.[CH2:23]([NH2:26])[CH2:24][NH2:25]>O1CCOCC1>[F:20][C:19]([F:22])([F:21])[C:16]1[CH:17]=[CH:18][C:13]([C:2]23[NH:26][CH2:23][CH2:24][N:25]2[C:9](=[O:11])[C:5]2[N:4]([CH:8]=[CH:7][CH:6]=2)[CH2:3]3)=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 67366612HCID 67366612, compound

Product 1

HCID 67368936HCID 67368936, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 1-{2-oxo-2-[5-(trifluoromethyl)pyridin-2-yl]ethyl}-1H-pyrrole-2-carboxylate (85 mg, 0.26 mmol) in 1,4-dioxane (20 mL) was added ethane-1,2-diamine (0.65 mL, 9.7 mmol). The solution was heated at reflux. After 4 days the reaction was complete (monitored by LCMS). The mixture was then concentrated in vacuo to give an oily solid. The material was purified by flash chromatography (Biotage SP4, 12 g cartridge, gradient CH2Cl21CV, 0-10% MeOH in CH2Cl2 10 CV) to give 10a-[5-(trifluoromethyl)pyridin-2-yl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (70 mg, yield: 85%). ESI-MI m/z [M+H]+ 323.0.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux
  3. concentrationThe mixture was then concentrated in vacuo
  4. customto give an oily solid
  5. customThe material was purified by flash chromatography (Biotage SP4, 12 g cartridge, gradient CH2Cl21CV, 0-10% MeOH in CH2Cl2 10 CV)

Sources & evidence

ORD record
ord-efe89d6d0a7a400e94db509aa8b6e262
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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