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-(3-methoxy-2-propoxybenzyl)-N-methylacrylamide 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-(3-methoxy-2-propoxybenzyl)-N-methylacrylamide (0.19 g, 0.42 mmol) in CH2Cl2 (5 mL) was treated with anhydrous HCl (0.42 mL of a 1.0 M solution in Et2O, 0.42 mmol). After stirring for 1 h, the mixture was diluted with Et2O (50 mL) and allowed to stir for 3 h. The solid was isolated by filtration, washed with Et2O and dried under vacuum at 50° C. for 3 d to give the title compound (0.17 g, 84%) as an off-white powder and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.94-10.92 (m, 1H), 10.47 (br s, 2H), 8.67-8.62 (m, 1H), 8.39-8.32 (m, 1H), 7.60-7.53 (m, 1H), 7.39-7.33 (m, 1H), 7.05-6.95 (m, 2H), 6.69-6.62 (m, 1H), 4.80-4.65 (m, 2H), 4.42-4.38 (m, 2H), 3.92-3.85 (m, 2H), 3.80 (s, 3H), 3.12-2.86 (m, 3H), 1.75-1.67 (m, 2H), 1.63-1.61 (m, 6H), 1.01-0.94 (m, 3H); MS (ESI) m/e 453 (M+H)+.

Provenance & Evidence