1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)-N-{[6-(trifluoromethyl)pyridin-3-yl]methyl}acetamide

Participants

Reaction Steps

N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.049 g, 0.254 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.050 g, 0.169 mmol) and (6-(trifluoromethyl)pyridin-3-yl)methanamine (0.033 g, 0.186 mmol) were combined and stirred together in dichloromethane (0.5 mL) at room temperature. After stirring overnight, the reaction was loaded directly onto a SF15-12 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 100% ethyl acetate/hexanes over 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 8.48 (s, 1H), 7.53-7.61 (m, 2H), 7.22-7.30 (m, 10H), 6.50-6.56 (m, 1H), 4.32 (d, J=6.1 Hz, 2H), 4.06 (s, 2H), 3.51 (t, J=6.4 Hz, 2H), 2.81 (t, J=6.4 Hz, 2H); MS (ESI−) m/z 452 (M−H)−.

Provenance & Evidence