4-Chlorobenzylamine → N-(4-Chlorobenzyl)-3,7-dimethyl-2-(morpholin-4-ylmethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 3,7-dimethyl-2-(morpholin-4-ylmethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate (Preparation 28, 700 mg) and 4-chloro-benzylamine (1.25 mL) is heated to 190° C. under a nitrogen atmosphere for 1 h. The reaction mixture is allowed to cool briefly and methanol (10 mL) is added. After cooling to room temperature, the product is filtered and washed with methanol and diethyl ether to afford 634 mg of the title compound as a white solid. Physical characteristics. M.p. 222-224° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.67, 8.66, 7.41-7.33, 4.52, 3.92, 3.67, 3.59, 2.51, 2.47; MS (ESI+) m/z 446 (M+H)+. Anal. Found: C, 59.11; H, 5.47; N, 9.32; Cl, 7.96; S, 7.17.

Provenance & Evidence