3-Methyl-5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine (0.040 g, 0.110 mmol, see Example 15), (R)-4-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)-4-methylpentanoic acid (0.0412 g, 0.120 mmol, Example 12), HOBT-H2O (0.0235 g, 0.153 mmol), and EDCI (0.0273 g, 0.142 mmol) were placed in DCM (5 mL) at room temperature. DIEA (d 0.742; 0.0954 mL, 0.548 mmol) was then added, and the reaction was stirred at room temperature for 18 hours. The reaction was then poured into saturated Na2CO3 and extracted with DCM. The combined organic fractions were dried, filtered, concentrated and purified (500:5 DCM:MeOH) to give (R)-tert-butyl 4-(4-chlorophenyl)-2-methyl-5-(4-(3-methyl-5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-5-oxopentan-2-ylcarbamate (0.040 g, 59.3% yield).
