1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-{[6-(acetylamino)pyridin-3-yl]ethynyl}-4-methyl-N-{4-[(4-methylpiperazin-1-yl)methyl]-3-(trimethylsilyl)phenyl}benzamide

Participants

Reaction Steps

To a solution of 3-{[6-(acetylamino)pyridin-3-yl]ethynyl}-4-methylbenzoic acid (0.22 mmol) in dry pyridine (5 mL) is added 4-(4-methylpiperazin-1-ylmethyl)-3-trimethylsilylaniline (60 mg, 0.22 mmol) and EDCI (62 mg, 0.325 mmol). The resulting mixture is stirred at r.t. overnight. The solvent is removed on rotavap and the residue is partitioned between DCM and aq. NaHCO3. The combined organic layers from extraction are dried (Na2SO4), filtered, concentrated, and the resulting residue is purified by silica gel flash chromatography [eluted with 5% MeOH (pre-saturated with NH3) in DCM] to give the desired product.

Provenance & Evidence