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-ethyl-benzofuran-2-ylmethyl)-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-ethyl-benzofuran-2-ylmethyl)-N-methylacrylamide (59.0 mg, 0.136 mmol) in CH2Cl2 (4 mL) and CH3OH (0.3 mL) was treated with anhydrous HCl (0.068 mL of a 2 M solution in Et2O, 0.136 mmol). After stirring for 1 h, the mixture was diluted with Et2O (5 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 (63.0 mg, 99%) as an off-white solid and as a mixture of amide rotamers: 1H NMR (500 MHz, DMSO-d6) δ 10.9 (s, 1H), 10.5 (br s, 2H) 8.71-8.60 (m, 1H), 8.39 (d, J=8.0 Hz, 1H), 7.65-7.50 (m, 3H), 7.35-7.20 (m, 3H), 4.80-5.01 (m, 2H), 4.40 (s, 2H), 3.20-2.90 (m, 3H), 2.77 (d, J=7.0 Hz, 2H), 1.62 (s, 6H), 1.22 (t, J=7.0 Hz, 3H); ESI MS m/z 433 (M+H)+.

Provenance & Evidence