Trifluoroacetic acid → HCID 73213799, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (S)-tert-butyl (1-((4-((4-methoxybenzyl)amino)-6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (100 mg, 0.145 mmol) in DCM (10 mL) at rt was added TFA (4 mL, 51.9 mmol) dropwise and the reaction was heated at 45° C. for 12 h. After the completion of reaction, the volatile organics were evaporated under reduced pressure and the residue obtained was purified by prep. HPLC (0.1% TFA in water/acetonitrile as mobile phase) to yield (S)-4-amino-8-((2-amino-4-methylpentyl)oxy)-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (16 mg, 0.046 mmol, 32% yield) as a mono TFA salt as an off white solid. LC/MS (ESI) m/e 341.2 [(M+H)+, calcd for C19H25N4O2 341.2]; LC/MS retention time (method B): tR=1.08 min; HPLC retention time (method A): tR=8.02 min; HPLC retention time (method B): tR=8.40 min; 1H NMR (400 MHz, MeOD) δ 8.44 (d, J=8.80 Hz, 1H), 8.00 (d, J=7.20 Hz, 1H), 7.71 (d, J=7.20 Hz, 1H), 7.24 (d, J=2.40 Hz, 1H), 7.21-7.22 (m, 1H), 4.51 (dd, J=3.20, 10.80 Hz, 1H), 4.34 (dd, J=6.40, 10.40 Hz, 1H), 3.84 (s, 3H), 3.78-3.82 (m, 1H), 1.65-1.89 (m, 3H), 1.08 (d, J=4.40 Hz, 3H), 1.06 (d, J=4.40 Hz, 3H).

Provenance & Evidence