2,4,6-Trimethylpyridine → Pnu-183792

Participants

Reaction Steps

A solution of N-(4-chlorobenzyl)-6-(hydroxymethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide from the product of Example 2 (140 mg), collidine (0.061 mL), and DMAP (8.1 mg) in 6.7 mL anhydrous DMF is cooled to 0° C. Methanesulfonyl chloride (0.12 mL) is added dropwise. The reaction is stirred at room temperature for approx. 2-3 hrs. 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 are combined and condensed to afford 70.1 mg (42%) of the title compound as a white solid.

Provenance & Evidence