Trifluoroacetic acid → HCID 71727015, compound

Participants

Reaction Steps

To a stirred solution of (S)-tert-butyl (1-((2-acetamido-7-methoxy-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (111 mg, 0.088 mmol) in dichloromethane (2 mL) was added TFA (0.027 mL, 0.352 mmol) dropwise and the reaction mixture was stirred at room temperature for 12 h. After completion of reaction, the volatiles were removed under reduced pressure to afford a residue which was purified by prep. HPLC (Sunfire C18 3.5 um, 19×150 mm column and 10 mM ammonium acetate in water) to yield (S)—N-(8-((2-amino-4-methylpentyl)oxy)-7-methoxy-5H-chromeno[3,4-c]pyridin-2-yl)acetamide (10 mg, 0.022 mmol, 25% yield) as white solid. 1H NMR (400 MHz, MeOD) δ 8.38 (s, 1H), 8.17 (s, 1H), 7.6 (d, J=8.8 Hz, 1H), 6.88 (d, J=8.8 Hz, 1H), 5.18 (s, 2H), 3.9 (s, 3H), 2.2 (s, 3H), 1.94 (m, 3H), 1.86-1.81 (m, 1H), 1.70-1.65 (m, 1H), 1.63-1.55 (m, 1H), 1.04 (m, 6H); LCMS (ESI) m/e 386.2 [(M+H)+, calcd for C21H28N3O4 386.2]; LC/MS retention time (Method E): tR=1.99 min; HPLC retention time (method A): tR=8.80 min; HPLC retention time (method B): tR=9.73 min.

Provenance & Evidence