Trifluoroacetic acid → HCID 68328510, compound

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 4-(6-(5-(5-(4-methoxybenzylamino)-1,3,4-thiadiazol-2-yl)-1-tosyl-1H-indol-3-yl)pyridin-2-yl)-1-methylpiperazin-2-one (350 mg, 0.515 mmol) in p-dioxane (6 mL) followed by aq. 1 M KOH (2.5 mL, 2.500 mmol). The reaction was stirred and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 80° C. for 15 min. The mixture was diluted with H2O and extracted with DCM. The combined organic layers were dried, filtered and concentrated to give the crude product. MS (ESI, pos. ion) m/z: 526 (M+1). A glass microwave reaction vessel was charged with crude 4-(6-(5-(5-(4-methoxybenzylamino)-1,3,4-thiadiazol-2-yl)-1H-indol-3-yl)pyridin-2-yl)-1-methylpiperazin-2-one (271 mg, 0.516 mmol) and TFA (5.00 mL, 67.3 mmol). The reaction was stirred and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 120° C. for 40 min, then the solvent was removed. The residue was purified with RP-HPLC to give 4-(6-(5-(5-amino-1,3,4-thiadiazol-2-yl)-1H-indol-3-yl)pyridin-2-yl)-1-methylpiperazin-2-one (88.0 mg, 0.217 mmol, 42.1%). MS (ESI, pos. ion) m/z: 406 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.70 (1H, d, J=2.0 Hz), 8.79 (1H, d, J=1.6 Hz), 8.11 (1H, d, J=2.5 Hz), 7.71 (1H, dd, J=8.4, 1.8 Hz), 7.59 (1H, t, J=7.9 Hz), 7.50 (1H, d, J=8.6 Hz), 7.27 (2H, s), 7.22 (1H, d, J=7.4 Hz), 6.62 (1H, d, J=8.2 Hz), 4.12 (2H, s), 4.06 (2H, t, J=5.4 Hz), 3.58 (2H, t, J=5.3 Hz), 2.96 (3H, s).

Provenance & Evidence