Cesium carbonate → 1-Methyl-4-(3-((5-methyl-2-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)thiazol-4-yl)methyl)phenyl)piperazin-1-ium trifluoroacetate

Participants

Reaction Conditions

Reaction Steps

Synthesized according to a procedure similar to the following: 5-(4-(3-bromobenzyl)-5-methylthiazol-2-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole was reacted with Cs2CO3 (2 molar equivalents), XPhos (0.4 molar equivalents), Pd2(dba)3 (0.2 molar equivalents), and N-methylpiperazine were placed in a microwave reaction vessel and dioxane (1 mL), which had been degassed by bubbling N2 through it for 10 min, was added. The reaction was heated by microwave irradiation at 120° C. for 1 h and purified by prep-HPLC (MeCN/H2O 40%-80% MeCN, containing 0.1% TFA) (4.5 mg, 11%). MS (ES+) C25H24F3N5O2S requires: 515, found: 516 [M+H]+; 1H-NMR (600 MHz, CD3OD) δ ppm 8.24 (d, J=7.2 Hz, 2H), 7.48 (d, J=7.2 Hz, 2H), 7.22 (t, J=6.0 Hz, 1H), 6.99 (s, 1H), 6.82-6.90 (m, 2H), 4.18 (s, 2H), 3.81 (d, J=13.2 Hz, 2H), 3.57 (d, J=13.2 Hz, 2H), 3.24 (t, J=12.0 Hz, 2H), 3.02 (t, J=12.0 Hz, 2H), 2.95 (s, 3H), 2.57 (s, 3H).

Provenance & Evidence