2,4,6-Trimethylpyridine → N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Participants

Reaction Steps

Methanesulfonyl chloride (0.23 mL, 3.0 mmol) was added to a mixture of N-(4-chlorobenzyl)-2-(hydroxymethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (446 mg, 1.19 mmol), collidine (0.39 mL, 3.0 mmol) and DMAP (22 mg, 0.18 mmol) in DMF (21 mL). The reaction was stirred at room temperature for 1 hour 15 minutes, going to an orange/amber solution. The reaction was cooled in an ice bath before diluting with water to a total volume of 100 mL. The mixture was stirred vigorously for 5 minutes before the solid precipitate was collected by filtration, washed with water and dried in vacuo, leaving the title compound as a white solid (460 mg).

Provenance & Evidence