Dimethylformamide → HCID 58081201, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (5-aminomethyl-4,6-dimethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (4.50 g, 17.90 mmol), propiolic acid (0.918 ml, 14.92 mmol), DIPEA (7.82 ml, 44.8 mmol) in DCM (140 ml) at 23° C. was added dropwise over 5 min 50% propylphosphonic anhydride in DMF (12.5 ml, 21.41 mmol). The reaction was stirred at 23° C. for 1 day. The reaction was quenched by addition of brine, and the phases were separated. The aqueous phase was further extracted with DCM, and the combined organic phase was dried over Na2SO4, filtered, and evaporated to provide the crude product, which was purified by flash column chromatography (silica gel 0.040-0.063 mm, 160 g, flow rate 60 ml/min, detection at 220 nm, MeOH in DCM 0->1% over 10 min, then 1->5% over 20 min) to yield the title compound. HPLC (Method G) Rt=1.333 min; MS (Method F) [M+H]+=304.31.

Provenance & Evidence