Diisopropylethylamine → 4-{(S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butyryl}-piperazin-1-sulphonic acid (1-methyl-piperidin-4-yl)-amide

Participants

Reaction Steps

A solution of 500 mg (0.90 mmol) (S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butanoic acid and 320 mg (1.00 mmol) TBTU in 0.2 mL (1.14 mmol) ethyldiisopropylamine and 50 mL THF was stirred for 1 h at RT. Then 270 mg (1.03 mmol) piperazin-1-sulphonic acid-(1-methyl-piperidin-4-yl)-amide and 5 mL DMF were added. The reaction solution was stirred overnight at RT. The reaction mixture was diluted with 50 mL EtOAc, extracted with 30 mL 15% K2CO3 solution and the organic phase was dried over Na2SO4. After the desiccant and solvent had been eliminated the residue was purified by chromatography (silica gel, gradient: DCM to DCM/MeOH/NH3 10:9:1).

Provenance & Evidence