Hydrochloric Acid → (E)-N-(3-Chloro-2-propoxybenzyl)-3-(3,3-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methylacrylamide hydrochloride

Participants

Reaction Steps

A stirring solution of (E)-N-(3-chloro-2-propoxybenzyl)-3-(3,3-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methylacrylamide (0.300 g, 0.656 mmol) in CH2Cl2 (7 mL) under N2 was treated with anhydrous HCl (0.32 mL of a 2 M solution in diethyl ether, 0.64 mmol) After stirring for 7 h, the resulting solid was collected by filtration, washed with Et2O (100 mL) and then dried to yield the target compound (0.25 g, 79%) as an off white solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.93 (br s, 1H), 10.38 (br s, 2H), 8.66-8.63 (m, 1H), 8.37-8.28 (m, 1H), 7.62-7.54 (m, 1H), 7.44-7.32 (m, 2H), 7.19-7.02 (m, 2H), 4.87-4.69 (m, 2H), 4.41-4.37 (m, 2H), 3.94-3.87 (m, 2H), 3.16-2.89 (m, 3H), 1.83-1.76 (m, 2H), 1.61-1.59 (m, 6H), 1.05-0.99 (m, 3H); MS (APCI) m/e 457 (M+H)+.

Provenance & Evidence