Hydrochloric Acid → HCID 71233246, compound

Participants

Reaction Steps

Methyl 3-(2-(((1R,2R)-2-(((S)-1-(4-(trifluoromethyl)phenyl)piperidin-3-yl)amino)cyclohexyl)amino)oxazol-5-yl)benzoate (470 mg, 0.866 mmol) was dissolved in a mixed solvent of MeOH (3.5 mL) and THF (3.5 mL), then 2 M of aqueous LiOH (7 mL, 14 mmol) was added. The resultant mixture was stirred at rt for 16 h. LC/MS check showed the reaction was completed. The reaction was cooled in an ice-bath, 3 M HCl was added dropwise to adjust pH ˜3. The reaction mixture was concentrated. The resulting residue was purified using prep HPLC (Phenomenex Luna Axia, 5μ, 30×100 mm, 40-80% B, gradient over 10 min, hold at 80% B for 2 min). The desired fractions were concentraed to almost dryness, and the residue was lyophilized in CH3CN—H2O to afford the title compound (2 TFA salt) as a beign colored powder (465 mg, 0.615 mmol, 71.0% yield). Anal. Calcd. for C28H31F3N4O3 m/z 528.2, found: 529.1.

Provenance & Evidence