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

Participants

Reaction Steps

A suspension of (E)-N-(3-ethyl-benzofuran-2-ylmethyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide (100 mg, 0.247 mmol) in CH2Cl2 (3 mL) and CH3OH (0.5 mL) was treated with anhydrous HCl (0.123 mL of a 2M solution in Et2O, 0.247 mmol). After stirring for 1 h, the mixture was diluted with Et2O (3 mL) and stirred for 10 minutes. The solid was isolated by filtration, washed with Et2O and dried under vacuum at 50° C. overnight to give the title compound (81.0 mg, 81%) as an off-white solid and as a mixture of amide rotamers: 1H NMR (500 MHz, DMSO-d6) δ 10.0 (br s, 2H), 8.82-8.75 (m, 1H), 8.33-8.27 (m, 1H), 7.68-7.55 (m, 3H), 7.50 (t, J=7.5 Hz, 1H), 7.33-7.24 (m, 3H), 5.01-4.81 (m, 2H), 4.26 (s, 2H), 3.84 (s, 2H), 3.20-2.92 (m, 3H), 2.78-2.74 (m, 2H), 1.23-1.19 (m, 3H); ESI MS m/z 405 (M+H)+.

Provenance & Evidence