N'-Hydroxy-4-(trifluoromethyl)benzene-1-carboximidamide → 3,3-Bis(4-fluorophenyl)-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 (0.204 g, 1.0 mmol), 2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid (Example 58D, 0.331 g, 1.0 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.383 g, 2.00 mmol) were stirred together in dichloroethane (5.0 mL) at room temperature for 2 hours under nitrogen. The reaction was then heated to 85° C. and stirred overnight. The reaction mixture was cooled, concentrated, loaded onto a SF25-40 column (Analogix®, Burlington, Wis.) and the product eluted using a gradient of 10% ethyl acetate/hexanes to 70% ethyl acetate over 30 minutes (Flow=30 mL/minute) to give the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 8.10 (d, J=8.1, 2H), 7.75 (d, J=8.3, 2H), 7.44-7.31 (m, 4H), 7.08-6.94 (m, 4H), 4.90 (s, 2H), 3.57 (t, J=6.5, 2H), 2.84 (t, J=6.5, 2H); MS (DCI) m/z 500.1 (M+H)+.

Provenance & Evidence