Methylamine → 2',4'-Difluoro-N-(3-(1-hydroxy-2-(methylamino)ethyl)phenyl)biphenyl-4-sulfonamide

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Reaction Steps

Using a method analogous to Method D, using 2′,4′-difluoro-N-(3-(oxiran-2-yl)phenyl)biphenyl-4-sulfonamide and 33% methylamine in ethanol, a mixture of regioisomers was obtained. This solution was evaporated and the isomers were separated by flash chromatography (SiO2, eluting with 5% to 20% methanol/DCM, containing 0.1% concentrated aqueous NH3), giving ABD789 as a light orange powder (165 mg). With further elution (increasing the polarity slowly to 40% methanol/DCM) ABD783 was obtained as an orange gum, which was triturated with ether to give the title compound as a light orange powder (330 mg). 1H NMR (400 MHz, DMSO-d6): δ 2.47 (3H, s), 2.70-2.76 (1H, t), 2.80-2.89 (1H, dd), 4.85 (1H, d, J=8 Hz), 6.95-7.15 (2H, m), 7.10-7.25 (3H, m), 7.40 (1H, t), 7.55-7.65 (1H, m), 7.66 (2H, d, J=8 Hz) and 7.84 (2H, d, J=8 Hz). MS, m/z: Calcd, 418.11. Found, 418.28 (M).

Provenance & Evidence