Methanedione--ethanol (1/1) → (S)-N-(4-(Chlorodifluoromethoxy)phenyl)-6-((3,4-dihydroxybutyl)amino)-5-(1H-pyrazol-5-yl)nicotinamide

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The title compound was prepared by chiral separation (Preparative chiral SFC, ChiralPak® AD-H, 250×30 mm, mobile phase: CO2/EtOH (3:2), flow rate: 50 mL/min, back pressure: 100 bar, column temperature: 38° C., wavelength: 220 nm, cycle time: 6.0 min) of a racemic mixture of N-(4-(chlorodifluoromethoxy)phenyl)-6-((3,4-dihydroxybutyl)amino)-5-(1H-pyrazol-5-yl)nicotinamide (Example 100), faster eluting isomer (Peak 1). Or alternatively in an analogous fashion to that described in Example 97 using (S)-benzyl(3,4-dihydroxybutyl)carbamate (Stage 101.1) as chiral starting material. Analytical chiral SFC (ChiralPak® AD-H, 250×4.6 mm, 5 μm, eluent: CO2/EtOH+0.05% DEA (3:2), flow rate: 2.4 mL/min, back pressure: 100 bar, temperature: 35° C., 220 nm): tR=3.18 min.

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