Butoxyacetic acid → N-(Butoxyacetyl)-3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonamide

Participants

Reaction Conditions

Reaction Steps

CDI (1,1′-carbonyl-diimidazole, 129.5 mg, 0.80 mmol) was added to a solution of butoxyacetic acid (103.8 μL, 0.80 mmol) in dry THF (4 mL). The mixture was stirred at 50° C. for 2.5 h. A solution of 3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonamide (see Example 1(f) above; 100 mg) and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene, 19.9 μL, 0.133 mmol) in dry THF (4 mL) was added to the reaction mixture. The reaction mixture was then stirred overnight at 50° C. MeOH (20 mL) was added to the reaction mixture, which was then concentrated in vacuo. The residue was dissolved in EtOAc (100 mL) and then washed with water (3×50 mL). The organic phase was dried and evaporated. The crude product was purified by column chromatography using 10% MeOH in CHCl3 as eluent to give the title compound (27 mg, 0.057 mmol).

Provenance & Evidence