[NH2:1][C:2]1[N:3]=[C:4](S(C)(=O)=O)[S:5][C:6]=1[C:7]#[N:8].[C:13]([NH:20][CH2:21][CH2:22][NH2:23])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].CCN(C(C)C)C(C)C.O>CS(C)=O.C(OCC)(=O)C>[C:16]([O:15][C:13](=[O:14])[NH:20][CH2:21][CH2:22][NH:23][C:4]1[S:5][C:6]([C:7]#[N:8])=[C:2]([NH2:1])[N:3]=1)([CH3:19])([CH3:17])[CH3:18]2.2 g (7.22 mmol) of 4-amino-2-(methylsulfonyl)-1,3-thiazole-5-carbonitrile (Example 14A) were dissolved in 24 ml of DMSO, and 1.74 g (10.84 mmol) of N-Boc-ethylenediamine and 933 mg (7.22 mmol) of DIEA were added. The mixture was stirred for 16 h at 120° C., and water and ethyl acetate were added once the reaction had ended. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulfate and purified by silica gel chromatography. This gave 633 mg (31% of theory) of the product.
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