Acetic Acid → HCID 118417117, compound

Participants

Reaction Steps

Dissolve tert-butyl 2-(1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)ethylcarbamate (220 mg, 0.76 mmol) in DCM (3 mL) and add trifluoroacetic acid (1 mL, 13.23 mmol). Stir at ambient temperature for 30 minutes. Concentrate the mixture under reduced pressure, then dissolve in 1,2-dichloroethane (20 mL). Add N-[(1S)-2,2,2-trifluoro-1-(4-formylphenyl)-ethyl]-methanesulfonamide (150 mg, 0.53 mmol), acetic acid (0.05 mL, 0.87 mmol), and sodium triacetoxyborohydride (642.3 mg, 3.03 mmol). Stir the mixture at ambient temperature overnight. Concentrate under reduced pressure to give a residue and dilute the residue with MeOH (2 mL). Purify the residue via preparatory TLC using 10% MeOH in DCM to give a colorless oil. Dissolve the oil in MeOH (3 mL) and add HCl (1M in diethyl ether; 0.5 mL, 0.5 mmol) and stir for 30 minutes. Concentrate under reduced pressure to give the title compound as a white solid (10 mg, 3.7%). MS (m/z): 456 (M-Cl).

Provenance & Evidence