Methylamine → HCID 178482482, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl(1-(4-(6-(bis(methylthio)methylene)-5-oxo-3-phenyl-5,6,7,8-tetrahydroquinolin-2-yl)phenyl)cyclobutyl)carbamate (100 mg, 0.18 mmol) in ethanol (873 μl) was added methylamine (2M in THF, 87 μl, 0.18 mmol) and the mixture heated to 80° C. under a nitrogen atmosphere for 2 hours. Further methylamine (2M in THF, 873 μl, 1.746 mmol) was added and the mixture heated to 80° C. under a nitrogen atmosphere for 2 hours. Hydrazine monohydrate (25.4 μl, 0.52 mmol) was added and the mixture heated to 80° C. for 18 hours. The reaction mixture was concentrated to dryness under reduced pressure and purified via Biotage chromatography (silica, DCM: MeOH, gradient elution from 100:0 to 90:10) to give a colourless solid (47 mg, 52% yield). 1H-NMR (500 MHz, CDCl3) δ 7.63 (1H, s), 7.32 (2H, d), 7.27 (2H, d), 7.16-7.22 (3H, m), 7.09-7.16 (2H, m), 5.06 (1H, br s), 3.10 (2H, t), 2.68 (3H, s), 2.22-2.60 (6H, br m), 1.97-2.09 (1H, m), 1.72-1.84 (1H, m), 1.03-1.53 (9H, br m). LCMS (Method A) RT=5.34 min, M+H+=522.19.

Provenance & Evidence