2,4,6-Trimethylpyridine → HCID 178522870, compound

Participants

Reaction Steps

A solution of N-(4-chlorobenzyl)-4-hydroxy-6-(hydroxymethyl)-3-quinolinecarboxamide from Example No. 166 (1.0 g), collidine (0.45 mL), and DMAP (60.0 mg) in 50 mL anhydrous DMF is cooled to 0° C. Methanesulfonyl chloride (0.25 mL) is added dropwise. The reaction is stirred at room temperature for approx. 2-3 h. Morpholine (0.34 mL) is added. The product is precipitated by addition of H2O. The crude product is adsorbed onto silica and chromatographed eluting with 2% MeOH in CH2Cl2. Fractions homogenous by TLC were combined and condensed to afford 352 mg of the title compound as a white solid.

Provenance & Evidence