Diisopropylethylamine → (s)-6-fluoro-10-[3-(3-methoxy-propyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene

Participants

Reaction Conditions

Reaction Steps

Combine 6-fluoro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride (0.304 g, 1.07 mmol), (S)-2-(3-methoxy-propyl)-piperazine (0.339 g, 2.14 mmol), and diisopropylethyl amine (0.19 mL, 1.07 mmol) in a mixture of toluene (3 mL) and dimethylsulfoxide (1 mL) and stir at 110° C. for 24 hours. Evaporate the mixture then purify by flash chromatography, eluting with a step gradient starting with dichloromethane going to 5% 2N ammonia-methanol in dichloromethane gives (s)-6-fluoro-10-[3-(3-methoxy-propyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene (0.110 g, 0.283 mmol, 26%) as a yellow oil. Mass spectrum (APCI): m/z=389.1 (M+1).

Provenance & Evidence