Pyridine → HCID 10365176, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (E)-2-(6-aminopyridin-3-yl)-N-(5-chlorothiazol-2-yl)-3-cyclopentylacrylamide (EXAMPLE 75, 50 mg, 143 μmol) in anhydrous CH2Cl2 (3 mL) was treated with pyridine (570 μL, 7.1 mmol) and MsCl (170 μL, 2.2 mmol). After stirring for 3 d at 20° C., the reaction mixture was diluted with Et2O (40 mL), before being extracted with 1M NaOH-saturated aqueous NaHCO3 (1:1, 2×15 mL). The combined aqueous extracts were neutralised with 2M HCl, before being extracted with EtOAc (2×50 mL). The combined organic extracts were washed with brine (20 mL), before being dried (MgSO4). Filtration, solvent evaporation, and column chromatography (1:1 IH-EtOAc) furnished the title compound: RTA=3.73 min; m/z (ES+)=427.2 [M+H]+.

Provenance & Evidence