[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:14][C:13](=S)[C:12]3[CH:11]=[C:10]([CH3:16])[S:9][C:8]=3[NH:7][C:6]=2[CH:17]=1.FC(F)(F)S(OC)(=O)=O.[CH3:27][O:28][CH2:29][CH2:30][C@H:31]1[CH2:36][NH:35][CH2:34][CH2:33][NH:32]1>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:14]=[C:13]([N:35]3[CH2:34][CH2:33][NH:32][C@@H:31]([CH2:30][CH2:29][O:28][CH3:27])[CH2:36]3)[C:12]3[CH:11]=[C:10]([CH3:16])[S:9][C:8]=3[NH:7][C:6]=2[CH:17]=1Suspend 6-fluoro-2-methyl-4,9-dihydro-3-thia-4,9-diazabenzo[f]azulene-10-thione (500 mg, 1.9 mmol) in dichloromethane (30 ml), stir under nitrogen and cool in an ice/water bath. Add methyl trifluoromethanesulfonate (500 μl), and stir overnight. Concentrate the reaction mixture under reduced pressure, take up in pyridine (10 ml) and add (S)-2-(2-methoxyethyl)piperazine (400 mg, 2.78 mmol) and stir the reaction mixture under nitrogen and heat at 90° C. for three days. Concentrate the reaction mixture under reduced pressure and purify by flash column chromatography on silica gel (eluent dichloromethane/methanol) to give the desired as a yellow solid 727 mg: Mass Spectrum (FIA) 375 (M+1).
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