Hydrazine hydrate (1:1) → HCID 178452588, compound

Participants

Reaction Steps

To a solution of tert-butyl(1-(4-(6-((dimethylamino)methylene)-7,7-dimethyl-5-oxo-3-phenyl-5,6,7,8-tetrahydroquinolin-2-yl)phenyl)cyclobutyl)carbamate (180 mg, 0.33 mmol) in anhydrous ethanol (4 mL) was added hydrazine hydrate (48 μL, 1 mmol). The reaction mixture was stirred at room temperature under a nitrogen atmosphere for 2 hours. The reaction mixture was concentrated to dryness under reduced pressure, purified by Biotage chromatography (silica, hexane:ethyl acetate, gradient elution from 99:1 to 60:40) and PREP HPLC (Method A) to give the desired product as a white solid (8 mg, 5% yield). 1H NMR (500 MHz, CDCl3) 8.12 (s, 1H), 7.27-7.48 (br m, 5H), 7.25-7.18 (br m, 5H), 5.03 (br s, 1H), 3.16 (s, 2H), 2.23-2.68 (br m, 4H), 1.97-2.12 (m, 1H), 1.75-1.88 (m, 1H), 1.11-1.57 (br s, 9H+6H). LCMS (Method A): RT=6.62 min, M+H+=521.

Provenance & Evidence