1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-{4-[5-(3-tert-Butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclohexanecarboxylic acid methyl ester

Participants

Reaction Steps

A mixture of N-(3-tert-butyl-phenyl)-6-piperazin-1-yl-nicotinamide (100 mg, 0.29 mmol) in CH2Cl2 (10 mL) was treated with trans-1,4-cyclohexane dicarboxylic acid monomethyl ester. (110 mg, 0.59 mmol) and EDCI (230 mg, 1.18 mmol) at room temperature. After stirring overnight the reaction mixture was partitioned between EtOAc and water. The organic layer was collected, dried over Na2SO4, filtered and concentrated. The residue was chromatographed on a silica gel column with 20-100% EtOAc in hexanes gradient to afford the product (120 mg, Yield: 80%). HRMS m/z calcd for C29H38N4O4 [M+H]+: 507.2966. Found: 507.2968.

Provenance & Evidence