Ethylenediamine → HCID 67370984, compound

HRID 1753154Notes

Reaction equation

HRID 1753154 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][N:10]2[CH:14]=[C:13]([C:15](=[O:19])[N:16]([CH3:18])[CH3:17])[CH:12]=[C:11]2[C:20]([OH:22])=O)=[CH:4][CH:3]=1.[CH2:24]([NH2:27])[CH2:25][NH2:26]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[NH:27][CH2:24][CH2:25][N:26]2[C:20](=[O:22])[C:11]2[N:10]([CH:14]=[C:13]([C:15]([N:16]([CH3:17])[CH3:18])=[O:19])[CH:12]=2)[CH2:9]3)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 67367064HCID 67367064, compound

Product 1

HCID 67370984HCID 67370984, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 1-[2-(4-chlorophenyl)-2-oxoethyl]-4-(dimethylcarbamoyl)-1H-pyrrole-2-carboxylic acid (90 mg, 0.27 mmol) in 1,4-dioxane (10 mL) was added ethane-1,2-diamine (0.1 mL, 1.5 mmol). The reaction mixture was heated at reflux 4 h (monitored by LCMS). The reaction mixture was then concentrated in vacuo to give an oil that was purified using flash chromatography (Biotage SP4, 12 g cartridge, 0-20% MeOH gradient in CH2Cl2) to give 10a-(4-chlorophenyl)-N,N-dimethyl-5-oxo-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazine-7-carboxamide as a light brown solid (26 mg, yield 27%) 1H NMR (400 MHz, d6-acetone): δ 2.75-2.84 (m, 1H), 2.95-3.21 (m, 6H), 3.33 (ddd, 1H, J 11.2, 7.7, 3.3 Hz), 3.49 (ddd, 1H, J 11.0, 7.7, 3.2 Hz), 3.72 (dt, 1H, J 11.0, 8.0 Hz), 4.41 (d, 1H, J 12.6 Hz), 4.75 (d, 1H, J 12.6 Hz), 7.01 (d, 1H, J 1.6 Hz), 7.13 (d, 1H, J 1.6 Hz), 7.26-7.35 (m, 4H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux 4 h (monitored by LCMS)
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. customto give an oil that
  5. customwas purified

Sources & evidence

ORD record
ord-137cb46f23664e258ce20421bb0dd47f
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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