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

Participants

Reaction Steps

Combine 6-fluoro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride (2.94 g, 10.35 mmol), (S)-2-piperazin-2-yl-ethanol (2.7 g, 20.7 mmol), diisopropylethylamine (3.6 mL, 20.7 mmol), dimethyl sulfoxide (4.25 mL) and toluene (17 mL) and heat to 110° C. for 42 hours. Cool to ambient temperature and dilute with ethyl acetate (200 mL). Wash with saturated sodium bicarbonate solution, brine and evaporate to give 2.64 g of the crude product. Silica gel chromatography, eluting with methylene chloride: acetonitrile: 7N NH3/methanol (85:10:7), gives 0.523 g of the title compound as a brown solid foam: mass spectrum (ion spray): m/z=361 (M+1).

Provenance & Evidence