Pyridine → HCID 46861610, compound

Participants

Reaction Conditions

Reaction Steps

With ice cooling, 85 μl of trifluoromethanesulphonic anhydride were added to a solution of 100 mg (0.25 mmol) of but-3-yn-1-yl(Z)-{6-[({[2-(methylamino)-2-oxo-1-phenylethylidene]amino}oxy)methyl]pyridin-2-yl}carbamate (only Z diastereoisomer) and pyridine (81 μl, 4 eq.) in acetonitrile (2 ml). The mixture was heated at 50° C. for 2 h and then cooled to room temperature. Then, 49 mg of sodium azide were added and the mixture was stirred again at 50° C. for 2 h. The homogeneous orange solution was then cooled to room temperature and filtered over silica gel, and the silica gel filter layer was washed with 50 ml of EtOAc. The combined organic phases were concentrated by evaporation in vacuo, giving 87 mg (84% purity) of (Z)-but-3-yn-1-yl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate.

Provenance & Evidence