Pioglitazone → HCID 54751748, compound

Participants

Reaction Steps

A solution of chloromethyl 2-(nitrooxy)ethylcarbamate (2, 13.37 g, 67.3 mmol) in CH2Cl2 (20 ml) is added drop-wise to a suspension of 5-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzyl)-thiazolidine-2,4-dione (pioglitazone, 12 g, 33.7 mmol) in CH2Cl2 (160 ml) and triethylamine (9.38 ml, 67.3 mmol) at 22° C. (room temperature) under an argon atmosphere. The reaction is stirred for 8 h. The reaction is diluted with CH2Cl2 and H2O and the layers separated. The organic layer is dried (MgSO4) and the solvent evaporated to give the crude product. The crude material is purified by column chromatography (silica, 40:60 ethyl acetate:heptane, product Rf 0.3 (80:20 ethyl acetate:heptane) to give the title compound (5-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzyl)-2,4-dioxothiazolidin-3-yl)methyl 2-(nitrooxy)ethylcarbamate (1), 5.3 g (30%), as a white solid.

Provenance & Evidence