2-Amino-thiazole-5-carboxylic acid ethyl ester → HCID 86594355, compound

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Reaction Steps

(E)-3-Cyclopentyl-2-(6-cyclopropylsulfanylpyridin-3-yl)acrylic acid (Preparation 15, 250 mg, 0.86 mmol) was condensed with ethyl 2-aminothiazole-5-carboxylate (297 mg, 1.73 mmol), using the method described in EXAMPLE 12, to furnish ethyl 2-[3-cyclopentyl-2-(6-cyclopropylsulfanylpyridin-3-yl)acryloylamino]thiazole-5-carboxylate: m/z (ES+)=444.3 [M+H]+. This ester was saponified, employing a procedure similar to that described in Step 3 of Preparation 16, to give 2-[3-cyclopentyl-2-(6-cyclopropylsulfanylpyridin-3-yl)acryloylamino]thiazole-5-carboxylic acid: m/z (ES+)=416.1 [M+H]+. Oxidation of this thioether, utilising an approach similar to that described in EXAMPLE 35, afforded 2-[3-cyclopentyl-2-(6-cyclopropanesulfonylpyridin-3-yl)acryloylamino]thiazole-5-carboxylic acid: m/z (ES+)=448.2 [M+H]+. This carboxylic acid (52 mg, 116 μmol) was condensed with MeNH2.HCl in the presence of NEt3, utilising the general procedure described in EXAMPLE 12, to give the title compound: RTA=3.29 min; m/z (ES+)=461.3 [M+H]+.

Provenance & Evidence