Hydrochloric Acid → (E)-3-(3,3-Dimethyl-2,3-dihydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide hydrochloride

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Reaction Steps

A solution of (E)-3-(3,3-dimethyl-2,3-dihydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide (0.11 g, 0.27 mmol) in CH2Cl2 (10 mL) was treated with anhydrous HCl (0.27 mL of a 1.0 M solution in Et2O, 0.27 mmol). After stirring for 15 min, 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. overnight to give the title compound (0.10 g, 86%) as a yellow powder and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ13.16-13.13 (m, 1H), 9.67-9.65 (m, 1H), 8.96-8.92 (m, 1H), 8.69 (s, 1H), 8.64-8.61 (m, 1H), 7.58-7.24 (m, 6H), 5.00-4.80 (m, 2H), 4.54 (br s, 2H), 3.19-2.92 (m, 3H), 2.27 (s, 3H), 1.36 (br s, 6H); MS (ESI) m/e 403 (M+H)+.

Provenance & Evidence