Potassium Carbonate → N-[(4-chlorophenyl)methyl]-7-(2-diethylaminoethyl)-2-(3-hydroxypropyl)-4-oxo-thieno[2,3-b]pyridine-5-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(4-chlorobenzyl)4-hydroxy-2-(3-hydroxypropyl)thieno[2,3-b]pyridine-5-carboxamide (Example No. 8) (0.300 g) in DMF (4 mL) are added K2CO3 (0.550 g) and 2-bromo-N,N-diethylethylamine hydrobromide (0.623 g). The reaction is heated to 90° C. and stirred for 3 d. An additional 0.220 g of K2CO3 and 0.415 g of 2-bromo-N,N-diethylethylamine hydrobromide are added. The reaction is stirred at 90° C. for 6 h. The reaction mixture is concentrated in vacuo, and the resulting residue is partitioned between CH2Cl2 (25 mL) and H2O (25 mL). The aqueous layer is extracted with CH2Cl2 (3×25 mL). The combined organic layers are dried with MgSO4, filtered and concentrated in vacuo. The resulting yellow oil is purified via column chromatography (CH2Cl2:CH3OH; 98:2, 95:5). Fractions homogeneous by TLC are combined and concentrated in vacuo to yield a yellow oil. This material is dissolved in methanolic HCl and then concentrated in vacuo. The residue is recrystallized twice from ethyl acetate/methanol to yield 0.078 g (19%) of the title compound as an off-white, crystalline solid.

Provenance & Evidence