Lithium Hydroxide → HCID 178438092, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl trans-4-{[6-chloro-5-(3-cyano-4-fluorophenyl)-1H-imidazo[4,5-b]pyridin-2-yl]oxy}cyclohexanecarboxylate (30 mg, 0.075 mmol) in DMSO (400 μL) was added cesium carbonate (48.9 mg, 0.150 mmol) and 3-methylazetidin-3-ol (2.55 mg, 0.150 mmol). The reaction was heated to 90° C. over 4 h. The reaction was cooled, then quenched with citric acid, and extracted with EtOAc. LiOH (100 μL, 0.200 mmol) was added and the reaction was stirred overnight. The reaction was then quenched with citric acid (2 mL, 10% w/v) and extracted with EtOAc (2×5 mL). The organic layers were combined and concentrated in vacuo to give a crude residue, which was purified via reverse phase HPLC to afford the title compound as white powder. LC-MS: calculated for C24H24ClN5O4 481.2, observed m/e: 482.1 (M+H)+ (Rt 0.8/2 min).

Provenance & Evidence