N,N-Diethylethylenediamine → 5-formyl-4-methyl-1 H-pyrrole-2-carboxylic acid (2-diethylamino-ethyl)-amide

HRID 1359682Notes

Reaction equation

HRID 1359682 reaction equation
[CH:1]([C:3]1[NH:7][C:6]([C:8]([OH:10])=O)=[CH:5][C:4]=1[CH3:11])=[O:2].Cl.CN(C)CCCN=C=N.ON1C2C=CC=CC=2N=N1.[CH2:32]([N:34]([CH2:37][CH2:38][NH2:39])[CH2:35][CH3:36])[CH3:33]>CN(C=O)C>[CH2:32]([N:34]([CH2:35][CH3:36])[CH2:37][CH2:38][NH:39][C:8]([C:6]1[NH:7][C:3]([CH:1]=[O:2])=[C:4]([CH3:11])[CH:5]=1)=[O:10])[CH3:33]

Participants

6

Reactant 4

HCID 60993N,N-DiethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 98988845-formyl-4-methyl-1H-pyrrole-2-carboxylic AcidHCID 21899179Dimethylaminopropyl carbodiimide hydrochloride

Product 1

HCID 98563405-formyl-4-methyl-1 H-pyrrole-2-carboxylic acid (2-diethylamino-ethyl)-amideYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid (2.50 g, 16.32 mmol) in DMF (54 mL) was added 1-ethyl-3-(3-dimethylamino-propylcarbodiimide hydrochloride (EDC, 3.76 g, 19.59 mmol), 1-hydroxybenzotriazole (HOBt, 2.65 g, 19.59 mmol) followed by diethylaminoethyl amine (2.75 mL, 19.59 mmol). The reaction solution was stirred for 12 h, and then DMF solvent was removed. The residue was purified on a silica gel column eluting with 1-5% methanol in dichloromethane to provide 3.2 g (78%) of 5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid (2-diethylamino-ethyl)-amide.

Workup

  1. customDMF solvent was removed
  2. customThe residue was purified on a silica gel column
  3. washeluting with 1-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-17c0ac49b97e49a6939934a188779b13
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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