Toluene → HCID 10115737, compound

Participants

Reaction Steps

Preparation of N-(4-Chlorobenzyl)-7-methyl-2-(4-morpholinylmethyl)-4-thioxo-4,7-dihydrothieno[2,3-b]pyridine-5-carbothioamide, (A-2 of Chart A) A-1 (570 mg, 1.32 mmol) was dissolved in dichloroethane (80 mL) followed by the addition of KHMDS (0.5 M, 2.64 mL, 1.32 mmol, 1 equiv.). Then Lawesson's reagent (1.1 g, 2.64 mmol, 2.0 equiv.) and toluene (80 mL) was added and the resulting mixture was heated at reflux for 6 h. The reaction was cooled to rt, diluted with dichloromethane, washed with water, Na2CO3, brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (heptane/EtOAc 1/1, ¼, 0/1 then DCM/MeOH 19/1) to afford 248 mg of crude N-(4-chlorobenzyl)-7-methyl-2-(4-morpholinylmethyl)-4-thioxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboamide and 139 mg of crude N-(4-chlorobenzyl)-7-methyl-2-(4-morpholinylmethyl)-4-thioxo-4,7-dihydrothieno[2,3-b]pyridine-5-carbothioamide A-2. The crude A-2 was purified by multiple silica gel chromatography (heptane/EtOAc 1/1, ¼, 0/1 then DCM/MeOH 1/0, 50/1, 19/1) to afford 55 mg (9%) of pure tan solid.

Provenance & Evidence