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1-(4-Aminophenyl)cyclopentanecarbonitrile-d8 is an intermediate used in the synthesis of Apatinib-d8 Hydrochloride (A726152), which is a labelled Apatinib (A726150). Apatinib is an orally available, small molecule multitargeted tyrosine kinase inhibitor. Apatinib selectively inhibits the vascular endothelial growth factor receptor-2 (VEGFR2). Apatinib functions by inhibiting VEGF-mediated endothelial cell migration and proliferation thus blocking new blood vessel formation in tumor tissue. Recent studies have shown that Apatinib enhances the efficacy of conventional chemotherapeutical drugs in side population (SP) cells and ABCB1-overexpressing leukemia cells.

1-(4-Aminophenyl)cyclopentanecarbonitrile is synthesised using 1-(4-nitrophenyl)cyclopentanecarbonitrile as a raw material by chemical reaction. The specific synthesis steps are as follows:
General procedure: The kilogram-scale reaction was performed in a 50 L single-deckglass reactor with the following conditions: 3 m (3 kg, 6.3 mol), FeO(OH)/C (460 g, 0.63 mol, 0.1 equiv), ethanol (20 L) and 80% N2H4H2O(800 g, 12.6 mol, 2 equiv) were added to a 50 L single-deck glass reactorat N2 atmosphere, then rising up the temperature to 75 C. The reactantwas stirred at 75 C for about 5 h. After the reaction was finished, the FeO(OH)/C catalyst was filtered off and washed with dichloromethane(5 L). The solvents were removed in vacuo and dried overnight byvacuum drying oven to get off-white powder 4m (2.67 kg, 6 mol), withHPLC purity >99.5%, yield 92.5%.