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Chemical synthesis of amine intermediate 4 and AP22408. DMF, dimethylformamide; BH3/THF, borane-tetrahydrofuran; Boc2O di-tert-butyl dicarbonate; Boc, tert-butoxycarbonyl; NBS, N-bromosuccinimide; n-BuLi, n-butyllithium; THF, tetrahydrofuran; CO2, carbon dioxide; HOBt, 1-hydroxybenzotriazole; EDC, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride; TFA, trifluoroacetic acid; Ac2O, acetic anhydride; TMSI, iodotrimethylsilane; Me, methyl; Et, ethyl.
