2-Amino-thiazole-5-carboxylic acid ethyl ester → (E)-ethyl 2-[2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acryloylamino]thiazole-5-carboxylate

Participants

Reaction Steps

Ethyl 2-aminothiazole-5-carboxylate (0.73 g, 4.26 mmol) was condensed with (E)-2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acrylic acid (Preparation 25, 0.33 g, 1.07 mmol), using the procedure described in EXAMPLE 65, to give (E)-ethyl 2-[2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acryloylamino]thiazole-5-carboxylate: m/z (ES+)=465.3 [M+H]+. This ester (0.50 g, 1.07 mmol) was saponified, employing the protocol described in EXAMPLE 127, to furnish (E)-2-[2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acryloylamino]thiazole-5-carboxylic acid: m/z (ES−)=435.2 [M−H]−. Utilising the approach described in EXAMPLE 129, this acid (0.16 g, 0.37 mmol) was transformed into the title compound: RTA=2.87 min; m/z (ES+)=450.2 [M+H]+.

Provenance & Evidence