Methanol → Carbon Dioxide

Participants

Reaction Steps

To 3-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-phenylamino)-cyclobutanecarboxylic acid (230 mg, 0.501 mmol) was added methanol (5.0 mL) and thionyl chloride (37 μl, 0.501 mmol) before it was stirred at ambient temperature for 30 min; the reaction mixture was concentrated, and the diastereomers were separated via SFC (Column: ChiralPak AS-H, Mobile Phase: liquid CO2/20% MeOH with diethylamine; then Column: Princeton Pyridine, Mobile Phase: liquid CO2/12% MeOH) to give methyl cis-3-((3-fluoro-4-(5-(1-phenyl-cyclopropyl)[1,3]thiazolo[5,4-b]pyridin-2-yl)phenyl)amino)-cyclobutanecarboxylate. MS (ESI) m/z: Calculated: 473.2; Observed: 474.1 (M++H).

Provenance & Evidence