1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)-N-(1,3-thiazol-2-ylmethyl)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 thiazol-2-ylmethanamine (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 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 7.69 (d, J=3.3 Hz, 1H), 7.19-7.38 (m, 11H), 6.77 (t, J=5.8 Hz, 1H), 4.67 (d, J=5.8 Hz, 2H), 4.09 (s, 2H), 3.53 (t, J=6.5 Hz, 2H), 2.84 (t, J=6.5 Hz, 2H); MS (ESI+) m/z 392 (M+H)+.

Provenance & Evidence