Ethylenediamine → HCID 67366902, compound

HRID 1753188Notes

Reaction equation

HRID 1753188 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:17]([O:19]C)=O)[N:5]([CH2:7][C:8]([C:10]2[CH:15]=[N:14][C:13]([CH3:16])=[CH:12][N:11]=2)=O)[CH:6]=1.[CH2:21]([NH2:24])[CH2:22][NH2:23]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:17](=[O:19])[N:23]3[CH2:22][CH2:21][NH:24][C:8]3([C:10]3[CH:15]=[N:14][C:13]([CH3:16])=[CH:12][N:11]=3)[CH2:7][N:5]2[CH:6]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 67367203HCID 67367203, compound

Product 1

HCID 67366902HCID 67366902, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 4-bromo-1-[2-(5-methylpyrazin-2-yl)-2-oxoethyl]-1H-pyrrole-2-carboxylate (111 mg, 0.33 mmol) in 1,4-dioxane (2 mL) was added ethane-1,2-diamine (0.6 mL, 9.0 mmol). The solution was heated at reflux. After 2 days the reaction was complete (monitored by LCMS). The mixture was then concentrated in vacuo to give a oily solid. The material was purified by flash chromatography (Biotage SP4, 12 g cartridge, gradient CH2Cl2 1 CV, 0-10% MeOH in CH2Cl2 15 CV and hold 10% MeOH 5 CV) to give 7-bromo-10a-(5-methylpyrazin-2-yl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (33 mg, yield 29%). 1H-NMR (400 MHz, CDCl3): δ 2.53 (s, 3H), 2.95 (dt, 1H, J 10.8, 7.9 Hz), 3.31 (ddd, 1H, J 11.0, 7.6, 3.8 Hz), 3.37 (ddd, 1H, J 11.3, 7.7, 3.8 Hz), 3.94 (dt, 1H, J 11.2, 7.8 Hz), 4.16 (d, 1H, J 12.0 Hz), 4.77 (d, 1H, J 12.0 Hz), 6.51 (d, 1H, J 1.6 Hz), 6.87 (d, 1H, J 1.7 Hz), 8.34 (d, 1H, J 1.4 Hz), 8.40-8.41 (m, 1H).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux
  3. concentrationThe mixture was then concentrated in vacuo
  4. customto give a oily solid
  5. customThe material was purified by flash chromatography (Biotage SP4, 12 g cartridge, gradient CH2Cl2 1 CV, 0-10% MeOH in CH2Cl2 15 CV and hold 10% MeOH 5 CV)

Sources & evidence

ORD record
ord-1cddabadd08d4405bba57a53d86454d6
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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