Diisopropylethylamine → 6-(6-Chloro-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid [4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-amide

Participants

Reaction Steps

A solution of 2.2 mMol 6-(6-chloropyrimidin-4-yloxy)-naphthalene-1-carbonyl chloride (Step 19.3) in 15 ml CH2Cl2 is added to a stirred solution of 410 mg (2.0 mMol) 4-(4-methyl-piperazin-1-ylmethyl)-phenylamine and 680 μl (4.0 mMol) diisopropylethylamine in 15 ml CH2Cl2. After 30 min, the reaction mixture is poured into a mixture of NaHCO3 and CH2Cl2. The aq. phase is separated off and extracted with CH2Cl2. The combined organic layers are washed with water and brine, dried (Na2SO4) and concentrated to give the crude product which is purified by column chromatography (SiO2; CH2Cl2/EtOH/NH3 95:4.5:0.5) to afford the title compound as a yellow powder.

Provenance & Evidence