反应详情

温度

100 °C

To a solution of N-(4-chlorobenzyl)4-hydroxy-2-(3-hydroxy-1-propynyl)-thieno[2,3-b]pyridine-5-carboxamide (Example No. 5) (0.250 g) in DMF (3 mL) is added K2CO3 (0.278 g) and bromoacetic acid (0.279 g). The reaction is heated to 100° C. and stirred for 18 h. An additional 0.200 g of bromoacetic acid is added and the reaction is stirred for an additional 18 h. The reaction mixture is concentrated in vacuo, and the resulting residue is dissolved in 10% NaOH and washed with CH2Cl2. The aqueous layer is acidified with conc. HCl and the resulting precipitate is filtered. This material is recrystallized 3 times from methanol to yield 0.068 g (24%) of the title compound as a tan solid.

1. stirringthe reaction is stirred for an additional 18 h
2. concentrationThe reaction mixture is concentrated in vacuo
3. dissolutionthe resulting residue is dissolved in 10% NaOH
4. washwashed with CH2Cl2
5. filtrationthe resulting precipitate is filtered
6. customThis material is recrystallized 3 times from methanol