Br[C:2]1[N:3]=[CH:4][S:5][C:6]=1[NH:7][C:8](=[O:10])[CH3:9].C([O-])([O-])=O.[Cs+].[Cs+].N#N.C[NH:20][C@@H:21]1CCC[CH2:23][C@H:22]1[NH:27][CH3:28].CC1N=CNC=1>CN(C=O)C.[Cu]I>[CH3:23][C:22]1[N:27]=[CH:28][N:20]([C:2]2[N:3]=[CH:4][S:5][C:6]=2[NH:7][C:8](=[O:10])[CH3:9])[CH:21]=1N-(4-bromothiazol-5-yl)acetamide from example 1.5 (1 g, 4.52 mmol), CuI(869 mg, 4.52 mmol) and Cs2CO3 (2.9 g, 9.1 mmol) were combined in a flask (backfilled with N2). Trans-N,N′-dimethylcyclohexane-1,2-diamine (630 mg, 4.52 mmol) and 4-methyl-1H-imidazole (446 mg, 5.4 mmol) in DMF (10 mL) were added and the mixture was stirred at 90° C. overnight. After the mixture was cooled to room temperature, the mixture was filtered through a syringe filter (washed with DMF). The filtrate purified by prep-HPLC to give 200 mg of the pure title compound (yield: 20%).
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