Pyridine → 2-(4-pyridin-3-yl-1,3-thiazol-2-yl)-1H-benzimidazole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-(3-pyridyl)-1,3-thiazole-4-carboxylic acid (300 mg) in pyridine (5 mL) and DMF (5 mL) at ambient temperature was added CDI (248 mg). The mixture was heated at 40° C. for 2 hours, treated with 2,3-diaminobenzamide dihydrochloride (326 mg), stirred at ambient temperature for 16 hours and concentrated. The concentrate was heated in glacial acetic acid (20 mL) at 110° C. for 2 hours, cooled and concentrated. The concentrate was partitioned between ethyl acetate and sodium bicarbonate solution, and the solid that precipitated was filtered and washed with water and ethyl acetate. 1H NMR (DMSO-d6) δ 7.38 (t, J=7.8 Hz, 1H), 7.60-7.67 (m, 1H), 7.78 (d, J=7.8 Hz, 1H), 7.81 (brs, 1H), 7.90 (dd, J=7.46, 1.0 Hz, 1H), 8.44-8.50 (m, 1H), 8.74-8.76 (m, 1H), 8.74 (s, 1H), 9.29 (brs, 1H), 9.34 (d, J=1.7 Hz, 1H), 13.44 (brs, 1H).

Provenance & Evidence