Diisopropylethylamine → tert-Butyl 4-(5-bromo-1,3,4-thiadiazol-2-yl)piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

DIPEA (430 μL, 2.460 mmol) was added to a stirred solution of 2,5-dibromo-1,3,4-thiadiazole (300 mg, 1.230 mmol) and tert-butyl piperazine-1-carboxylate (275 mg, 1.476 mmol) in dioxane (4 mL). The reaction mixture was heated at 120° C. for 2 hours. The reaction mixture was cooled to room temperature, filtered under vacuum, rinsed with dioxane, and the filtrate was concentrated in vacuo to afford the crude product as an orange oily residue. The crude material was purified by preparative HPLC under neutral conditions (ammonium formate modified) to afford the title compound as a yellow solid (331 mg, 77% yield). LC-MS: Rt 1.18 min; MS m/z 351.1 [M+2]+ [Method A]. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.38-3.55 (m, 8H), 1.41 (s, 9H).

Provenance & Evidence