Hydrochloric Acid → HCID 77174803, compound

Participants

Reaction Steps

The crude 5-(3,3-diethoxypropylamino)thieno[3,2-b]pyridin-7-yl benzoate from above (677.3 g, 1.68 mol) was dissolved in 3.0 L of THF. Then, 12N HCl (1.68 mol, 0.14 L) was added dropwise while the reaction temperature was maintained below 20° C. with an ice-water bath. After stirring for 5 minutes, solids precipitated. The resultant mixture was stirred at room temperature for 1 h, followed by the addition of ethyl acetate (2.0 L). The mixture was stirred for 30 min. The solids were filtered, rinsed with ethyl acetate (250 ml×2), and then dried under reduced pressure at 55° C. to give the title compound 5-(3-oxopropylamino)thieno[3,2-b]pyridin-7-yl benzoate HCl salt as a light brown solid. 1H NMR (400 MHz, DMSO d6) δ 2.20 (m, 2H), 3.56 (m, 2H), 6.31 (t, 1H, J=3.6 NHz), 7.83-7.87 (m, 2H), 7.96 (d, 1H, J=6.0 Hz), 8.16-8.20 (m, 2H), 8.35 (d, 1H, J=5.6 Hz), 10.20 (s, 1H).

Provenance & Evidence