Réaction #2859

ord-e34502d7c6c04c4ba22048fd23ff4bf0

Équation de réaction

CCOC(C)=O
EtOAc
CI
methyl iodide
[H-].[Na+]
sodium hydride
N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4nc(Cl)ccc4s3)C2=O)c1
5-Chlorothieno[3,2-b]pyridine-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide
CN([C@H]1CCN(Cc2cccc(C#N)c2)C1=O)S(=O)(=O)c1cc2nc(Cl)ccc2s1
title compound
CN([C@H]1CCN(Cc2cccc(C#N)c2)C1=O)S(=O)(=O)c1cc2nc(Cl)ccc2s1
5-Chlorothieno[3,2-b]pyridine-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-methylamide

Solvants

Conditions de réaction

Température
0°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températureto warm to room temperature
  2. 2
    Autrethe layers are separated
  3. 3
    LavageThe organic layer is washed with 1N HCl, H2O, saturated NaHCO3 solution and saturated NaCl
  4. 4
    SéchageThe organic phase is then dried over MgSO4
  5. 5
    Filtrationfiltered
  6. 6
    Concentrationconcentrated

Mode opératoire

5-Chlorothieno[3,2-b]pyridine-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide (0.25 g, 0.56 mmol) is dissolved in 6 mL of DMF and cooled to 0° C. To the solution is added methyl iodide (0.40 g, 2.82 mmol) and sodium hydride (25 mg of a 60% dispersion in mineral oil, 0.62 mmol). The reaction mixture is allowed to warm to room temperature and is stirred for 2 h. At this time, the solution is diluted with and EtOAc and the layers are separated. The organic layer is washed with 1N HCl, H2O, saturated NaHCO3 solution and saturated NaCl. The organic phase is then dried over MgSO4, filtered and concentrated to give the title compound (0.25 g, 0.54 mmol) as a solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05731315uspto-grants-1998_03