1-Methylpiperazine → HCID 86711894, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(1-(3-bromobenzyl)-5-methyl-1H-1,2,4-triazol-3-yl)-5-(4-(trifluoromethoxy)phenyl)-1,3,4-oxadiazole (84 mg, 0.176 mmol), 1-methylpiperazine (28 μL, 0.26 mmol), NaOtBu (36.4 mg, 0.38 mmol), dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine (8.2 mg, 0.0176 mmol) and chloro-(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) (13.6 mg, 0.0176 mmol) in THF (1 mL) was degassed (freeze-pump-thaw, under N2). The reaction mixture was stirred at 65° C. for 2 h, and then the solvent was removed under reduced pressure. The crude reaction mixture was dissolved in DMSO and purified by pre-HPLC (Mobile phase: A=H2O, B=MeCN containing 0.1% TFA; Gradient: B=20%-50% in 12 min; Column: Waters C18) to afford 1-methyl-4-(3-((5-methyl-3-(5-(4-(trifluoromethoxy)phenyl)-1,3,4-oxadiazol-2-yl)-1H-1,2,4-triazol-1-yl)methyl)phenyl)piperazin-1-ium trifluoroacetate (1 mg, 1.1%) as a white solid. MS (ES+) C24H24F3N7O2 requires: 499. found: 500 [M+H]+; 1H-NMR (500 MHz, CD3OD) δ ppm 8.26 (d, J=8.9 Hz, 2H), 7.53 (d, J=8.9 Hz, 2H), 7.32 (t, J=7.6 Hz, 1H), 7.02-7.00 (m, 2H), 6.88 (d, J=7.4 Hz, 1H), 5.47 (s, 2H), 3.89-3.79 (m, 2H), 3.60-3.52 (m, 2H), 3.35-3.33 (m, 4H), 2.94 (s, 3H), 2.57 (s, 3H).

Provenance & Evidence