Potassium Carbonate → N-(4-Chlorobenzyl)-7-[2-(diethylamino)ethyl]-2-(3-hydroxy-1-propynyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide hydrochloride

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(4-chlorobenzyl)-4-hydroxy-2-(3-hydroxy-1-propynyl)thieno[2,3-b]pyridine-5-carboxamide (Example No. 5) (0.300 g) in DMF (4 mL) is added K2CO3 (0.334 g) and 2-bromo-N,N-diethylethylamine hydrobromide (0.420 g). The reaction is heated to 90° C. After 4.5 h, an additional 0.111 g of K2CO3 is added and the reaction is stirred at 90° C. for 3 d. An additional 0.210 g of 2-bromo-N,N-diethylamine hydrobromide and 0.111 g of K2CO3 are added and the reaction is stirred for an additional 5 h. The reaction mixture is added to H2O and then concentrated in vacuo. The resulting brown solid is purified via column chromatography (CH2Cl2:CH3OH; 98:2, 95:5). The resulting yellow solid is dissolved in methanolic HCl and concentrated in vacuo. The salt is recrystallized twice from ethanol to yield 0.080 g (20%) of the title compound as a pale yellow solid.

Provenance & Evidence