[2-(3-Cyclohexyl-3-phenethylureido)-thiazol-5-ylsulfanyl]-acetic acid → HCID 178472930, compound

Participants

Reaction Conditions

Reaction Steps

An equimolar mixture of 1,1-carbonyldiimidazole, (2-amino-thiazole-5-sulfonylamino)-acetic acid ethyl ester and DMAP (5 mol %) in THF was heated for 5 h at 50-60° C. and then cooled to room temperature. Then (3-methyl-butyl)-(4-methyl-cyclohexyl)-amine (1 equivalent; prepared following the procedure described in the preparation of [2-(3-cyclohexyl-3-phenethyl-ureido)-thiazol-5-ylsulfanyl]-acetic acid) was added and the reaction is stirred overnight at room temperature. The reaction mixture was quenched with water. The organic phase was isolated and the aqueous phase was extracted with CH2Cl2, and the combined organic phases were dried and concentrated in vacuo. The crude product was dissolved in MeCN and purified using HPLC to give {2-[3-(3-methyl-butyl)-3-(trans-4-methyl-cyclohexyl)-ureido]-thiazole-5-sulfonylamino}-acetic acid ethyl ester as crystals.

Provenance & Evidence