1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-[(1-methyl-1H-pyrazol-3-yl)methyl]-2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)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 (1-methyl-1H-pyrazol-3-yl)methanamine (0.021 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 SF10-8 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 0.4% to 7.5% methanol/dichloromethane over 20 minutes (flow=20 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.23-7.34 (m, 11H), 6.40 (t, J=6.0 Hz, 1H), 6.06 (d, J=2.2 Hz, 1H), 4.38 (d, J=5.3 Hz, 2H), 4.05 (s, 2H), 3.82 (s, 3H), 3.50 (t, J=6.4 Hz, 2H), 2.82 (t, J=6.4 Hz, 2H); MS (ESI−) m/z 387 (M−H)−.

Provenance & Evidence