Dimethylformamide → (+/-)-3-(7-Methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-oxo-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-2-yl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

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To a solution of (±)-2-hydroxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-1-one (130 mg, 0.26 mmol) and diisopropylethylamine (91 μL, 0.52 mmol) in dichloromethane (1 mL) at 0° C. was added 4-nitrophenyl-chloroformate (57.6 mg, 1.10 equiv). The ice bath was removed and stirring continued for 4 h. The reaction was treated with a solution of 3-(piperidin-4-yl)quinolin-2(1H)-one (88.9 mg, 1.50 equiv) and diisopropylethylamine (91 μL, 0.52 mmol) in dimethylformamide (1 mL). The reaction was stirred at room temperature overnight. The reaction was poured into water/dichloromethane. The mixture was extracted with dichloromethane (2×) which was washed with saturated sodium bicarbonate, then water (2×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (5% to 20% methanol/dichloromethane) gave 112 mg (57%) as an oil.

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