2-tert-Butyl-1,1,3,3-tetramethylguanidine → (cis)-Tert-butyl 4-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-8-yloxy)-5-fluoroazepane-1-carboxylate

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Reaction Conditions

Reaction Steps

trans-tert-Butyl 4-fluoro-5-(4-nitrophenylsulfonyloxy)azepane-1-carboxylate (0.526 g, 1.26 mmol) and 2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-8-ol (0.320 g, 1.14 mmol) were slurried in CH3CN (5.5 mL). To this mixture was added 2-tert-butyl-1,1,3,3-tetramethylguanidine (0.276 mL, 1.37 mmol) dropwise. The mixture was warmed to 40° C. and stirred overnight. The mixture was cooled to ambient temperature and diluted with water (10 mL) and stirred for 15 minutes, then filtered, and the solid was washed with water and hexanes and dried. This provided 0.460 g of the title compound (81%) as an off-white solid (>95% pure by HPLC). MS ESI (+) m/z 496.0 (M+1) detected.

Provenance & Evidence