Diisopropylethylamine → (S)-6-Fluoro-10-[4-methyl-3-(2-methylsulfanyl-ethyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene dihydrochloride

Participants

Reaction Steps

Heat a mixture of 6-fluoro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride salt (0.135 g, 0.476 mmol), (S)-1-methyl-2-(2-methylsulfanyl-ethyl)-piperazine (0.166 g, 0.95 mmol) and diisopropyl ethylamine (0.083 mL, 0.476 mmol) in DMSO (0.2 mL) and toluene (0.8 mL) at 110° C. for 46 hours. Dilute the reaction mixture with ethyl acetate and 0.1N sodium hydroxide solution. The ethyl acetate extract gives 0.196 g. of the crude product. Silica gel chromatography, eluting with methylene chloride:methanol (100:5), gives 0.081 g of the title compound as an orange oil. The dihydrochloride salt precipitates in ethyl acetate as an orange solid: mp 194° C.; mass spectrum (ion spray): m/z=405 (M+1).

Provenance & Evidence