Formaldehyde → (4-{Methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester

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Reaction Conditions

Reaction Steps

A solution of (4-{[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester (0.09 g, 0.2 mmol) in dioxane (1 mL) was treated with 1N NaH2PO3 solution (1 ml) and a 37% aqueous solution of formaldehyde (1 ml). The mixture was heated to 60° C. for 7.5 h. Additional dioxane (1 ml) was added and heated for 11.5 h. The mixture was extracted with aqueous saturated NaHCO3 solution/Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated to give 0.08 g (86%) of (4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester as yellow waxy solid, MS: 465 (MH+).

Provenance & Evidence