tert-butyl(1-(4-(3-hydroxy-2-methyl-8-phenyl-4,5-dihydro-3H-imidazo[4,5-f]quinolin-7-yl)phenyl)cyclobutyl)carbamate → 7-(4-(1-aminocyclobutyl)phenyl)-2-methyl-8-phenyl-4,5-dihydro-3H-imidazo[4,5-f]quinolin-3-ol

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Reaction Steps

tert-butyl(1-(4-(3-hydroxy-2-methyl-8-phenyl-4,5-dihydro-3H-imidazo[4,5-f]quinolin-7-yl)phenyl)cyclobutyl)carbamate (10 mg, 0.019 mmol) was dissolved in TFA (1 mL) and stirred for 30 seconds. The solution was immediately concentrated to dryness under reduced pressure. The residue was dissolved in diethyl ether (˜2 mL) and concentrated to dryness under reduced pressure three times. The residue was then slurried in diethyl ether (2 mL) and after settling the supernatant solvent removed by pipette. This was repeated three times. The remaining solvent was removed under reduced pressure and freeze-dried to give the desired product as a pale brown solid (10 mg, 80% yield). 1H-NMR (500 MHz, CD3OD) δ 7.92 (1H, s), 7.48 (2H, d), 7.43 (2H, d), 7.30-7.34 (3H, m), 7.22-7.26 (2H, m), 3.42 (2H, t), 3.18 (2H, t), 2.72-2.81 (2H, m), 2.63 (3H, s), 2.54-2.64 (2H, m), 2.18-2.29 (1H, m), 1.91-2.02 (1H, m). LCMS (Method A) RT=3.14 min, M+H+=423.12.

Provenance & Evidence