Lithium Hydroxide → HCID 178492745, compound

Participants

Reaction Steps

To a solution of (R)-ethyl 2-methoxy-6-(5-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)isonicotinate (Example 96, 50 mg, 0.1 mmol) in tetrahydrofuran (1.0 mL) was added a solution of lithium hydroxide (14.9 mg, 0.6 mmol) in methanol (1.0 mL) and water (1.0 mL). The resulting suspension was stirred at room temperature for 2 h. The mixture was concentrated under reduced pressure. To the residue was added a saturated solution of ammonium chloride in water (10 mL). The pH of the mixture was adjusted to 3 using aqueous hydrochloric acid (1N). The mixture was extracted with ethyl acetate (20 mL×3). The organics were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified via HPLC to afford the title compound. MS (ESI+) (M+H) 451.1; HPLC retention time 2.21 min (Method A).

Provenance & Evidence