Cesium carbonate → HCID 86619282, compound

Participants

Reaction Steps

To a solution of the compound of intermediate VII (2.36 g, 8.40 mmol) in DMF (160 mL) was added anhydrous cesium carbonate (8.32 g, 25.0 mmol) and 1,1-dimethylethyl 2-(bromomethyl)-4-thiomorpholinecarboxylate (enantiomer E1) (2.50 g, 8.40 mmol). After stirring at ambient temperature for 4 h, sat NH4Cl was added and the reaction was extracted with EtOAc. The combined organic extracts were washed with water, brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue subjected to flash chromatography (MeOH/CH2Cl2, silica gel) to give the 2.3 g of the desired compound contaminated with 1,1-dimethylethyl 7-{[2-(4-amino-1,2,5-oxadiazol-3-yl)-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-7-yl]oxy}tetrahydro-1,4-thiazepine-4-(5H)-carboxylate. This was used without further purification in the next step. MS (ES+) m/z 496 (M+H)+.

Provenance & Evidence