反应详情

A yellow solution of 2-(3-(6-isopropoxypyridin-2-yl)-1-tosyl-1H-indol-5-yl)-5-(methylsulfonyl)-1,3,4-thiadiazole (89.3 mg, 0.115 mmol) and (±)-tert-butyl 3-aminopiperidine-1-carboxylate (Combi-Blocks, Inc., San Diego, Calif.; 0.110 mL, 0.573 mmol) in dioxane (1.0 mL) was heated in an open microwave vial at 90° C. for 3.5 d. Chromatographic purification of the resulting dry residue (silica gel, 0-100% EtOAc/Hex) furnished tert-butyl 3-(5-(3-(6-isopropoxypyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-thiadiazol-2-ylamino)piperidine-1-carboxylate (38.6 mg, 0.056 mmol, 49%) as a yellow oil: MS (ESI, pos. ion) m/z: 689.2 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.79 (s, 1H), 8.07 (s, 2H), 7.92 (d, J=7.4 Hz, 1H), 7.82 (d, J=8.4 Hz, 4H), 7.59-7.64 (m, 2H), 7.29 (br. s., 1H), 6.61-6.65 (m, 1H), 5.55 (dt, J=12.5, 6.3 Hz, 1H), 3.69 (d, J=13.3 Hz, 2H), 3.48-3.59 (m, 1H), 3.41 (t, J=7.2 Hz, 2H), 2.36-2.39 (m, 2H), 2.35 (s, 3H), 1.55-1.57 (m, 2H), 1.46 (d, J=3.1 Hz, 6H), 1.44 (s, 9H).

1. customChromatographic purification of the resulting dry residue (silica gel, 0-100% EtOAc/Hex)