Hydrazine hydrate (1:1) → HCID 178452591, compound

Participants

Reaction Steps

To a solution of methyl 2-(4-(1-((tert-butoxycarbonyl)amino)cyclobutyl)phenyl)-5-oxo-3-phenyl-5,6,7,8-tetrahydroquinoline-6-carboxylate (60 mg, 0.11 mmol) in anhydrous ethanol (1500 μL) was added hydrazine monohydrate (9 μL, 0.19 mmol). The reaction mixture was heated to reflux under a nitrogen atmosphere for 18 hours. After cooling to room temperature the reaction mixture was concentrated to dryness under reduced pressure, purified by Biotage chromatography (silica, dichloromethane:methanol, gradient elution from 99:1 to 90:10) and slurried in diethyl ether (1 mL) to give the desired product as a white solid (19 mg, 33% yield). 1H-NMR (500 MHz, CD3OD) δ 7.94 (1H, s), 7.32 (2H, d), 7.21-7.29 (5H, m), 7.14-7.21 (2H, m), 3.18 (2H, t), 2.81 (2H, t), 2.31-2.50 (4H, m), 2.00-2.12 (1, br m), 1.76-1.91 (1H, br m), 1.09-1.48 (br m). LCMS (Method A) RT=5.57 min, M+H+=509.17.

Provenance & Evidence