Reaction #2859

Reaction equation

EtOAc

methyl iodide

sodium hydride

5-Chlorothieno[3,2-b]pyridine-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide

→

title compound

5-Chlorothieno[3,2-b]pyridine-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-methylamide

Solvents

DMF

Conditions

Workup

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

Procedure

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