Hydrazine → HCID 73214026, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-2-(1-((9-(2-hydroxypropan-2-yl)-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)isoindoline-1,3-dione (200 mg, 0.152 mmol) in ethanol (5 mL), was added hydrazine (4.76 μl, 0.152 mmol) at RT then the mixture was heated to 60° C. for 4 h. The reaction mixture was filtered, concentrated and purified by prep. HPLC to afford (S)-8-((2-amino-4-methylpentyl)oxy)-9-(2-hydroxypropan-2-yl)-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one as white solid (9 mg, 0.021 mmol, 14% yield). LC/MS (ESI) m/e 398.0 [(M+H)+, calcd for C23H32N3O3 398.2]; LC/MS retention time (method G): tR=1.99 min. HPLC retention time (method A): tR=8.63 min; HPLC retention time (method B): tR=9.79 min. 1H NMR (400 MHz, METHANOL-d4) ppm 0.94-1.10 (m, 6H), 1.25-1.37 (m, 1H), 1.49-1.78 (m, 7H), 1.82-1.93 (m, 1H), 2.96-3.19 (m, 2H), 3.56-3.65 (m, 1H), 3.80 (s, 3H), 4.16-4.29 (m, 1H), 4.34-4.49 (m, 1H), 7.01-7.15 (m, 1H), 8.10-8.22 (m, 1H), 8.51-8.64 (m, 2H).

Provenance & Evidence