N'-Hydroxy-4-(trifluoromethyl)benzene-1-carboximidamide → 3,3-Diphenyl-1-({3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}methyl)pyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A solution of (Z)—N-hydroxy-4-(trifluoromethyl)benzimidamide (0.579 g, 2.84 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.762 g, 2.58 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.594 g, 3.10 mmol) were stirred together in dichloroethane (0.5 mL) at room temperature for 2 hours. The reaction was then heated to 85° C. and stirred overnight. The reaction was cooled, loaded onto a SF25-40 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 30% ethyl acetate/hexanes over 30 minutes (flow=40 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 8.09-8.15 (m, 2H), 7.71-7.76 (m, 2H), 7.23-7.43 (m, 10H), 4.91 (s, 2H), 3.58 (t, J=6.5 Hz, 2H), 2.90 (t, J=6.4 Hz, 2H); MS (ESI−) m/z 462 (M−H)−.

Provenance & Evidence