1,2-Dichloroethane → HCID 22390967, compound

HRID 397404Notes

Reaction equation

HRID 397404 reaction equation
[CH:1]([C:3]1[NH:7][C:6]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:5][C:4]=1[CH3:13])=[O:2].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH3:13][C:4]1[CH:5]=[C:6]([CH2:8][CH2:9][C:10]([N:32]2[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]2)=[O:12])[NH:7][C:3]=1[CH:1]=[O:2]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 223909933-(5-Formyl-4-methyl-1H-pyrrol-2-yl)propanoic acid

Product 1

HCID 22390967HCID 22390967, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(5-formyl-4-methyl-1H-pyrrol-2-yl)-propionic acid (271.8 mg, 1.5 mmol) in DMF (4mL) was added HOBt (243.2 mg, 1.8 mmol), EDC (345.1 mg, 1.8 mmol) and then 1-methylpiperazine (0.2 mL, 1.8 mmol). The mixture was stirred at room temperature under nitrogen for overnight. The reaction was poured into sat. sodium bicarbonate (50 mL) and extracted with ethyl acetate. The combined organic layer was dried, concentrated and column chromatographed (MeOH/DCM) to give 325.2 mg (82%) of 3-methyl-5-[3-(4-methyl-piperazin-1-yl)-3-oxo-propyl]-1H-pyrrole-2-carbaldehyde as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe combined organic layer was dried
  3. concentrationconcentrated
  4. customcolumn chromatographed (MeOH/DCM)

Sources & evidence

ORD record
ord-c3adb884430c443a86d56d88c56576a5
Source dataset
uspto-grants-2003_08
Patent number
US06610688B2

Reaction notes

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