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

Participants

Reaction Conditions

Reaction Steps

A solution of (Z)—N-hydroxy-4-(trifluoromethyl)benzimidamide (0.142 g, 0.698 mmol), 2-(2-oxo-3-phenylpiperidin-1-yl)acetic acid (0.148 g, 0.634 mmol; Example 91D) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.158 g, 0.825 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 SF15-12 column (Analogix®) and the product eluted using a gradient of 5% ethyl acetate/hexanes to 100% ethyl acetate over 25 minutes (Flow=30 mL/minute). The residue was dissolved in ethyl acetate and concentrated to give the title compound. 1H NMR (300 MHz, CDCl3) δ 8.23 (d, J=8.2, 2H), 7.77 (d, J=8.3, 2H), 7.42-7.15 (m, 5H), 5.19 (d, J=16.7, 1H), 4.73 (d, J=16.7, 1H), 3.84-3.76 (m, 1H), 3.70 (ddd, J=5.3, 7.6, 12.7, 1H), 3.59 (dt, J=5.5, 11.2, 1H), 2.43-2.18 (m, 1H), 2.18-1.82 (m, 3H); MS (ESI+) m/z 402.0 (M+H)+.

Provenance & Evidence