Diisopropylethylamine → N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-(3-fluoroazetidin-1-yl)ethyl)imidazo[1,2-a]pyridine-3-carboxamide

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Reaction Steps

A solution of 3-fluoroazetidine hydrochloride (61 mg, 0.55 mmol) in DCM (2 mL) was treated at ambient temperature with Hunig's base (0.10 mL, 0.57 mmol). To the hazy solution was added N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-oxoethyl)imidazo[1,2-a]pyridine-3-carboxamide (prepared according to (Example 127, Steps A-B; 50 mg, 0.11 mmol) (prepared according to the procedure for Example 127) and the (10 equivalents) was added, followed by 2 drops of glacial acetic acid, and the resulting mixture was stirred at ambient temperature for 16 hours. The reaction mixture was quenched with saturated aqueous sodium bicarbonate solution, and extracted multiple times with DCM and EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to preparative thin-layer chromatography on silica, with a 10% MeOH-DCM mixture as eluent to afford the desired product (10 mg) as a white solid. MS (ES+APCI) m/z=512 (M+H) detected.

Provenance & Evidence