[F:1][C:2]([F:24])([F:23])[C:3]1[N:4]=[CH:5][C:6]([NH:9][C@H:10]2[CH2:14][CH2:13][CH2:12][C@@H:11]2[NH:15]C(=O)OC(C)(C)C)=[N:7][CH:8]=1.BrN1C(=O)CCC1=O.[ClH:33].O1CCOCC1>C(Cl)Cl>[ClH:33].[Cl:33][C:5]1[C:6]([NH:9][C@H:10]2[CH2:14][CH2:13][CH2:12][C@@H:11]2[NH2:15])=[N:7][CH:8]=[C:3]([C:2]([F:24])([F:23])[F:1])[N:4]=1To a solution of tert-butyl N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]carbamate (1.04 g, 3.00 mmol) in dry DCM (10 ml) at 0° C. under an atmosphere of nitrogen was added 1-bromopyrrolidine-2,5-dione (CAS number 128-08-5; 0.80 g, 4.50 mmol). The reaction was allowed to warm to room temperature and stirred for 17 hours and then was concentrated in vacuo. The resulting residue was purified by column chromatography (basic silica, 0-50% ethyl acetate/petrol). To this was then added HCl in 1,4-dioxane (4 M, 7.51 ml, 30.0 mmol) and stirred at room temperature for 72 hours. The reaction mixture was concentrated in vacuo and azeotropically distilled with toluene to afford the title compound.
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