Trifluoroacetic acid → 5-(3-(6-chloropyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 5-(3-(6-chloropyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (480 mg, 0.818 mmol) and TFA (2.0 mL). The mixture was stirred and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 120° C. for 20 min then the solvent was removed. The crude residue was treated with 1N NaOH and the resulting precipitate was collected to give 5-(3-(6-chloropyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (340 mg, 0.728 mmol, 89%) as a light yellow amorphous solid. MS (ESI, pos. ion) m/z: 466.9 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.43 (1H, s), 9.01 (1H, s), 8.84 (1H, s), 8.71 (1H, s), 8.18 (1H, d, J=8.8 Hz), 8.03 (2H, m, J=8.4 Hz), 7.85-7.93 (1H, m), 7.45 (2H, m, J=8.2 Hz), 7.28 (2H, s), 2.34 (3H, s).

Provenance & Evidence