Hydrochloric Acid → (E)-3-(3,3-Dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methyl-N-(3-methyl-benzo[b]thiophen-2-ylmethyl)acrylamide hydrochloride

Participants

Reaction Steps

A suspension of (E)-3-(3,3-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methyl-N-(3-methyl-benzo[b]thiophen-2-ylmethyl)acrylamide (0.15 g, 0.35 mmol) in CH2Cl2 (10 mL) was treated with anhydrous HCl in Et2O (0.35 mL, 1.0 M). After stirring for 5 min, the mixture was diluted with Et2O (50 mL) and allowed to stir for 1 h. The solid was isolated by filtration, washed with Et2O, and dried under vacuum at 60° C. for 4 d to give the title compound (0.16 g, 96%) as a light yellow powder and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.92 (s, 1H), 10.56 (br s, 2H), 8.66-8.67 (m, 1H), 8.40 (s, 1H), 7.86-7.89 (m, 1H), 7.73-7.75 (m, 1H), 7.58-7.63 (m, 1H), 7.30-7.40 (m, 3H), 4.90-5.13 (m, 2H), 4.39-4.41 (m, 2H), 2.94-3.17 (m, 3H), 2.43 (s, 3H), 1.63 (s, 6H); MS (ESI) m/e 435 (M+H)+.

Provenance & Evidence