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. Author manuscript; available in PMC: 2012 May 1.
Published in final edited form as: Bioorg Med Chem Lett. 2010 Nov 21;21(9):2740–2745. doi: 10.1016/j.bmcl.2010.11.082

Scheme 2.

Scheme 2

Synthesis of conjugates of pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amines with fluorescent moieties (9, 10, and 14) and other acyl derivatives using standard amide coupling protocols and click chemistry. Reagents and conditions: a) activated fluorophore (AlexaFluor 488 carboxylic acid, 2,3,5,6-tetrafluorophenyl ester for 9; 6-carboxytetramethylrhodamine succinimidyl ester for 10), DMF, 0.1M aq. solution of Na2B4O7 (pH = 8.5), rt, 20 h; 6-heptynoic acid, EDC·HCl, an. DMF : an. CH2Cl2 (1:1, v/v), rt, 16 h for 11; b) corresponding azide (PEG4 carboxamide-6-azidohexanyl biotin for 12, N-(2-azidoethyl)acetamide for 13, CuSO4·5H2O, sodium ascorbate, DMSO:H2O (1:1, v/v), rt 16 h; c) 6-(((4,4-difluoro-5-(2-pyrrolyl)-4-bora-3a,4a-diaza-s-indacene-3-yl)styryloxy)acetyl)aminohexanoic acid, succinimidyl ester (BODIPY 650/665-X), DMF, 0.1 M aq. Na2B4O7 (pH = 8.5), rt, 18 h.