Diisopropylethylamine → HCID 45274309, compound

Participants

Reaction Steps

To 1-(3-(trifluoromethyl)benzyl)piperazine (0.090 g, 0.368 mmol), 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.140 g, 0.368 mmol) and 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.099 g, 0.335 mmol) in dichloromethane (1.0 mL) was added diisopropylethylamine (0.088 mL, 0.502 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction was concentrated and loaded onto silica gel. The product was eluted using a gradient of 5% to 100% ethyl acetate/hexanes giving incomplete purification. A second chromatography over silica gel using a gradient of 0.5% to 5% methanol/dichloromethane gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.41-7.58 (m, 4H), 7.20-7.37 (m, 10H), 4.19 (s, 2H), 3.60 (t, J=4.8 Hz, 2H), 3.52 (t, J=6.5 Hz, 2H), 3.51 (s, 2H), 3.41 (t, J=4.8 Hz, 2H), 2.81 (t, J=6.5 Hz, 2H), 2.40 (t, J=4.9 Hz, 2H), 2.28 (t, J=4.8 Hz, 2H); MS (ESI−) m/z 520 (M−H)−.

Provenance & Evidence