5-(3-(6-ethoxypyrazin-2-yl)-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine → 5-(3-(6-ethoxypyrazin-2-yl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 5-(3-(6-ethoxypyrazin-2-yl)-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (68 mg, 0.148 mmol) in TFA (1 mL). The reaction was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 120° C. for 30 min, then the solvent was removed. The residue was purified with RP-HPLC (10-40% ACN in H2O with 0.1% TFA) and the fractions were combined and MeCN was removed in vacuo. The mixture was treated with sat. NaHCO3 and extracted with CHCl3/iPrOH (4:1). The combined organic layers were dried, filtered and concentrated to give 5-(3-(6-ethoxypyrazin-2-yl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine (18.5 mg, 0.055 mmol, 36.9% for two steps) as a yellow solid. MS (ESI, pos. ion) m/z: 339 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 11.94 (1H, br. s.), 8.80 (1H, d, J=1.6 Hz), 8.76 (1H, s), 8.37 (1H, d, J=2.5 Hz), 8.00 (1H, s), 7.76 (1H, dd, J=8.5, 1.7 Hz), 7.54 (1H, d, J=8.4 Hz), 7.27 (2H, s), 4.61 (2H, q, J=7.0 Hz), 1.53 (3H, t, J=7.0 Hz).

Provenance & Evidence