Ethylenediamine → HCID 67371585, compound

HRID 1910925Notes

Reaction equation

HRID 1910925 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][N:10]2[CH:14]=[CH:13][CH:12]=[C:11]2[C:15]([OH:17])=O)=[CH:4][CH:3]=1.[CH2:19]([NH2:22])[CH2:20][NH2:21]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[NH:22][CH2:19][CH2:20][N:21]2[C:15](=[O:17])[C:11]2[N:10]([CH:14]=[CH:13][CH:12]=2)[CH2:9]3)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 67368552HCID 67368552, compound

Product 1

HCID 67371585HCID 67371585, compoundYield 91.1%

Procedure

To a suspension of crude 1-[2-(4-bromophenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylic acid (1.1 g, 0.714 mmol) suspended in xylenes (50 mL) was added ethane-1,2-diamine (0.5 mL, 7.5 mmol). The orange reaction mixture was heated at reflux for 1 h. The reaction mixture was concentrated in vacuo to give a dark orange oil that was purified using flash chromatography (Biotage SP4, 40 g cartridge, 0-10% MeOH gradient in EtOAc) to give 10a-(4-bromophenyl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one as a pale yellow solid (216 mg, 90% yield). 1H NMR (400 MHz, d6-acetone): δ 2.71-2.84 (m, 1H), 3.30-3.38 (m, 1H), 3.42 (ddd, 1H, J 11.0, 7.7, 3.2 Hz), 3.70 (dt, 1H, J 10.8, 7.8 Hz), 4.36 (d, 1H, J 12.3 Hz), 4.65 (d, 1H, J 12.3 Hz), 6.03 (dd, 1H, J 3.7, 2.6 Hz), 6.66 (m, 2H), 7.29-7.33 (m, 2H), 7.45-7.49 (m, 2H).

Workup

  1. temperatureThe orange reaction mixture was heated
  2. temperatureat reflux for 1 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto give a dark orange oil that
  5. customwas purified

Sources & evidence

ORD record
ord-e6295d43a1074110a6a76d5f1bff950b
Source dataset
uspto-grants-2013_12
Patent number
US08604034B2

Reaction notes

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