Trifluoroacetic acid → HCID 16058857, compound

Participants

Reaction Steps

To a suspension of tert-butyl (S)-5-((R)-3-(7-methyl-1H-indazol-5-yl)-2-(4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxamido)propanamido)-6-oxo-6-(4-(pyridin-4-yl)piperazin-1-yl)hexylcarbamate (230 mg, 0.27 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (10 mL) at 0° C. After 1 h at room temperature, the solvent was removed under high vacuum and then dissolved in methanol. The free base of title compound was liberated by passing the methanolic solution over Strata-X—C-33μ cation polymeric sorbent followed by elution with 3.0 M ammonia solution in methanol to give N-((R)-1-((S)-6-amino-1-oxo-1-(4-(pyridin-4-yl)piperazin-1-yl)hexan-2-ylamino)-3-(7-methyl-1H-indazol-5-yl)-1-oxopropan-2-yl)-4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxamide as a white solid in 72% yield. 1H-NMR (CD3OD) δ 8.08-8.07 (m, J=2, 2H), 7.95 (s, 1H), 7.61 (d, J=10 Hz, 1H), 7.51-7.44 (m, 3H), 7.29 (d, J=10 Hz, 1H), 7.23-7.19 (m, 1H), 7.11 (s, 1H), 6.79-6.78 (m, 2H), 4.80-4.77 (m, 2H), 4.60-4.55 (m, 1H), 4.11-4.04 (m, 2H), 3.82-3.80 (m, 2H), 3.66-2.78 (m, 11H), 2.51 (s, 3H), 1.87-1.11 (m, 11H; MS (ESI) 747 (M+H); Rf=1.64.

Provenance & Evidence