Triethylamine → HCID 178520141, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxypropyl)-3-quinolinecarboxamide from Example 110 (0.23 g), Et3N (0.090 mL), and catalytic DMAP (5-10 mol %) in 20 mL DMF is cooled to 0° C. Bromoacetyl bromide (0.050 mL) is added in one portion. The reaction is stirred at 0° C. for 20 minutes, then at room temperature for 1.5 h. Once the reaction was complete, it is partitioned between CH2Cl2 and H2O. The aqueous layer is extracted 3× with CH2Cl2. The organics are combined, dried over Na2SO4, filtered, and concentrated under reduced pressure to give a liquid which subsequently crystallizes to an off-white solid when it is dried on the vacuum pump overnight. The solid is triturated in CH2Cl2 /hexanes, filtered, and dried to give the desired product (0.27 g, 0.53 mmol, 91%).

Provenance & Evidence