Ethylenediamine → HCID 67369880, compound

HRID 1753163Notes

Reaction equation

HRID 1753163 reaction equation
[Br:1][C:2]1[N:6]([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=O)[C:5]([C:18]([O:20]C)=O)=[CH:4][CH:3]=1.[CH2:22]([NH2:25])[CH2:23][NH2:24]>O1CCOCC1>[Br:1][C:2]1[N:6]2[CH2:7][C:8]3([C:10]4[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=4)[NH:25][CH2:22][CH2:23][N:24]3[C:18](=[O:20])[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3301Ethylenediamine2×HCID 67365424HCID 67365424, compound

Product 1

HCID 67369880HCID 67369880, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 5-bromo-1-[2-(4-methoxyphenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylate (250 mg, 0.71 mmol) in 1,4-dioxane (50 mL) was added ethane-1,2-diamine (1.0 mL, 15 mmol). The solution was heated at reflux one week. During that time a batch of ethane-1,2-diamine (1.5 mL, 22 mmol) was added. The mixture was concentrated in vacuo to give a oil that was partitioned between water (30 mL) and CH2Cl2 (30 mL). The aqueous layer was further extracted with CH2Cl2 (2×30 mL). The organic layers were dried (MgSO4), filtered and concentrated in vacuo to give a oil that was purified by flash chromatography (Biotage SP4, 12 g cartridge, gradient 0-10% methanol in CH2Cl2) to give 8-bromo-10a-(4-methoxyphenyl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one as a pale yellow solid (135 mg, yield 52%). ESI-MI m/z calculated [M+H]+ 364.0.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux one week
  3. concentrationThe mixture was concentrated in vacuo
  4. customto give a oil that
  5. customwas partitioned between water (30 mL) and CH2Cl2 (30 mL)
  6. extractionThe aqueous layer was further extracted with CH2Cl2 (2×30 mL)
  7. dry with materialThe organic layers were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a oil that
  11. customwas purified by flash chromatography (Biotage SP4, 12 g cartridge, gradient 0-10% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-2f8576de05be44c998e0ff285e8a18ee
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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