Ethylenediamine → HCID 67370081, compound

HRID 1753194Notes

Reaction equation

HRID 1753194 reaction equation
O=[C:2]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=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:16]1[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][CH:15]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 67367135HCID 67367135, compound

Product 1

HCID 67370081HCID 67370081, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 1-[2-oxo-2-(pyridin-4-yl)ethyl]-1H-pyrrole-2-carboxylate (55 mg, 0.23 mmol) in 1,4-dioxane (10 mL) was added ethane-1,2-diamine (0.6 mL, 9.0 mmol). The mixture was heated at reflux for 64 hours and then concentrated in vacuo to give a residue that was purified by flash chromatography (Biotage SP4, gradient CH2Cl2 3 CV, 0 to 10% methanol in CH2Cl2 10 CV, hold 10% MeOH 10 CV) to give 10a-(pyridin-4-yl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one as an off-white solid (35 mg, yield: 60%). 1H-NMR (400 MHz, CDCl3): δ 2.84 (dt, 1H, J 15.2, 4.4 Hz), 3.30-3.37 (m, 1H), 3.49 (ddd, 1H, J 11.3, 7.1, 3.5 Hz), 3.79 (dt, 1H, J 11.2, 8.0 Hz), 4.26 (d, 1H, J 12.2 Hz), 4.39 (d, 1H, J 12.3 Hz), 4.48 (dd, 1H, J 2.5, 1.6 Hz), 6.12 (dd, 1H, J 3.8, 2.6 Hz), 6.92 (dd, 1H, J 3.9, 1.5 Hz), 7.25-7.28 (m, 2H), 8.47-8.50 (m, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 64 hours
  3. concentrationconcentrated in vacuo
  4. customto give a residue that
  5. customwas purified by flash chromatography (Biotage SP4, gradient CH2Cl2 3 CV, 0 to 10% methanol in CH2Cl2 10 CV, hold 10% MeOH 10 CV)

Sources & evidence

ORD record
ord-97a5ce68f11a4f59868f5c317be8f882
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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