Ethylenediamine → 7-bromo-10a-(4-chlorophenyl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one

HRID 1910913Notes

Reaction equation

HRID 1910913 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:17]([OH:19])=O)[N:5]([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=O)[CH:6]=1.[CH2:20]([NH2:23])[CH2:21][NH2:22]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:17](=[O:19])[N:22]3[CH2:21][CH2:20][NH:23][C:8]3([C:10]3[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=3)[CH2:7][N:5]2[CH:6]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 673664304-bromo-1-[2-(4-chlorophenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylic acid

Product 1

HCID 584063827-bromo-10a-(4-chlorophenyl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-oneYield 68.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of crude 4-bromo-1-[2-(4-chlorophenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylic acid (100 mg, 0.29 mmol) dissolved in a mixture of xylenes (10 mL) and ethanol (3 mL) was added ethane-1,2-diamine (100 μL, 1.5 mmol). The reaction mixture was heated at reflux. After 90 minutes (monitored by LCMS) the mixture was concentrated in vacuo and the resultant residue purified flash chromatography (Biotage SP4, 40 g cartridge, 0-5% MeOH gradient in CH2Cl2) to give 7-bromo-10a-(4-chlorophenyl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one as a light yellow solid (73 mg, yield: 68%). 1H NMR (400 MHz, d6-acetone): δ 2.74-2.82 (m, 1H), 3.30-3.38 (m, 1H), 3.44 (ddd, 1H, J 7.7, 3.4, 1.3 Hz), 3.67-3.75 (m, 1H), 4.39 (d, 1H, J 12.5 Hz), 4.69 (d, 1H, J 12.5 Hz), 6.68 (d, 1H, 1.8 Hz), 6.79 (d, 1H, J 1.7 Hz), 7.32-7.40 (m, 4H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux
  3. concentrationAfter 90 minutes (monitored by LCMS) the mixture was concentrated in vacuo
  4. customthe resultant residue purified flash chromatography (Biotage SP4, 40 g cartridge, 0-5% MeOH gradient in CH2Cl2)

Sources & evidence

ORD record
ord-a3636d0420524449add455424edccc31
Source dataset
uspto-grants-2013_12
Patent number
US08604034B2

Reaction notes

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