N,N-Diethylethylenediamine → 5-(4-diethylamino-butyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester

HRID 2191498Notes

Reaction equation

HRID 2191498 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:23])=[C:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[NH:9][C:10]=1[CH2:11][CH2:12][CH2:13][CH2:14]Br)=[O:5])[CH3:2].[CH2:24]([N:26](CC)[CH2:27][CH2:28]N)[CH3:25]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:23])=[C:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[NH:9][C:10]=1[CH2:11][CH2:12][CH2:13][CH2:14][N:26]([CH2:27][CH3:28])[CH2:24][CH3:25])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 498404632-O-tert-butyl 4-O-ethyl 5-(4-bromobutyl)-3-methyl-1H-pyrrole-2,4-dicarboxylate

Product 1

HCID 592500695-(4-diethylamino-butyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(4-Bromo-butyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 60c (220 mg, 0.57 mmol) was dissolved in 5 ml of dichloromethane under stirring, and added with N,N-diethylethylenediamine (164 μl, 1.13 mmol) to the solution and refluxed for 30 minutes in an oil bath. The reaction mixture was concentrated to evaporate solvent and refluxed for another 1 hour. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was concentrated under reduced pressure, purified by silica gel column chromatography to obtain the title compound 5-(4-diethylamino-butyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-cert-butyl ester 4-ethyl ester 60d (187 mg, yield 78%) as a white solid.

Workup

  1. temperaturerefluxed for 30 minutes in an oil bath
  2. concentrationThe reaction mixture was concentrated
  3. customto evaporate solvent
  4. temperaturerefluxed for another 1 hour
  5. concentrationthe reaction mixture was concentrated under reduced pressure
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-7bc8ffbbbf97486689a9040daf3966ad
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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