反应详情

To a solution of N-(4-chlorobenzyl)-2-(hydroxymethyl)-7-methyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide (0.300 g) from Example No. 35 in DMF (17 mL) are added DMAP (16 mg), 2,4,6-collidine (0.27 mL), and methanesulfonyl chloride (0.16 mL). The reaction mixture is stirred at room temperature for 1 h and then synephrine (1.39 g) is added. The mixture is stirred at room temperature for 18 h and is then poured into water (50 mL). The resulting off-white solid is filtered off. Additional material precipitates out of the filtrate. The two lots of material are combined and purified by column chromatography (CH2Cl2, CH2Cl2/methanol, 99/1; 98/2; 96/4) to yield 0.253 g (60%) of the title compound as a white solid.

1. stirringThe mixture is stirred at room temperature for 18 h
2. filtrationThe resulting off-white solid is filtered off
3. customAdditional material precipitates out of the filtrate
4. custompurified by column chromatography (CH2Cl2, CH2Cl2/methanol, 99/1; 98/2; 96/4)