Toluene → HCID 5276327, compound

Participants

Reaction Steps

A mixture of N-(4-Chlorobenzyl)-9-(4-morpholinylmethyl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamide (1.20 g, 2.64 mmol) of preparation 6 is dissolved in dichloroethane (160 mL) followed by the addition of KHMDS (0.5 M, 5.3 mL, 2.64 mmol, 1 equiv.). Then Lawesson's reagent (2.1 g, 5.28 mmol, 2.0 equiv) and toluene (160 mL) is added and the resulting mixture is heated at reflux for 24 h. The reaction is cooled to room temperature, diluted with DCM, washed with water, brine, dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography (heptane/EtOAc 4/1, 1/1, 1/4, 0/1 then DCM/MeOH 19/1) and then repurified by silica gel chromatography (DCM/MeOH 11/0, 45/1, 9/1) to afford 48 mg of the title compound as a solid.

Provenance & Evidence