tert-Butyl (3-aminopropyl)carbamate → N-(5-(3-(2-fluorophenyl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-yl)-1,3-propanediamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(3-(2-fluorophenyl)-1-tosyl-1H-indol-5-yl)-5-(methylsulfonyl)-1,3,4-thiadiazole (0.053 g, 0.10 mmol) in p-dioxane (1 mL) was added tert-butyl 3-aminopropylcarbamate (88 mg, 0.50 mmol, Aldrich), and the reaction was heated at 90° C. for 8 h. The residue was then purified with RP-HPLC. The purified material was dissolved in dioxane (1 mL) and aq. NaOH (1M, 0.1 mL) was added. The solution was heated in a microwave at 120° C. for 10 min. The solution was concentrated under reduced pressure and the resulting oil was stirred with 4M HCl/dioxane for 30 min, then evaporated under reduced pressure. The residue was purified by preparative HPLC to give N-(5-(3-(2-fluorophenyl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-yl)-1,3-propanediamine (32 mg, 61.4%). MS (ESI, pos. ion) m/z: 368 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 8.10 (1H, s), 7.66-7.72 (1H, m), 7.62-7.66 (1H, m), 7.59 (1H, d, J=1.6 Hz), 7.53-7.57 (1H, m), 7.17-7.35 (3H, m), 3.57 (2H, t, J=6.7 Hz), 3.03-3.10 (2H, m), 2.04-2.11 (2H, m).

Provenance & Evidence