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

HRID 1839649Notes

Reaction equation

HRID 1839649 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-deb7fb83abc143a8a799f83d91bf10e4
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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