2-Methyl-5,10-dihydro-4H-thieno[2,3-b][1,5]benzodiazepine-4-thione → (S)-10-[3-(2-phenylsulfanyl-ethyl)piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diazabenzo[f]azulene

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Reaction Steps

Combine 2-methyl-4,9-dihydro-3-thia-4,9-diazabenzo[f]azulene-10-thione (0.455 g, 1.85 mmol), (S)-2-(2-phenylsulfanyl-ethyl)-piperazine (0.411, 1.85 mmol) and pyridine (5 mL) and reflux for 36 hours. Evaporate the mixture and apply the material to 10 g of SCX, then elute with methanol followed by 5% 2N ammonia-methanol in dichloromethane and then 2N ammonia-methanol. Purification by flash chromatography, eluting with a step gradient starting with dichloromethane going to 7% 2N ammonia-methanol in dichloromethane gives (S)-10-[3-(2-phenylsulfanyl-ethyl)-piperazin-1-yl]-2-methyl 4H-3-thia-4,9-diazabenzo[f]azulene (0.126 g, 0.290 mmol, 16%). Mass spectrum (APCI): m/z=435.1 (M+1).

Provenance & Evidence