CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:25]([NH:27][C:28]([NH:30][C:31]1[N:36]=[CH:35][C:34]([C:37]2[S:38][C:39]([C:42]([OH:44])=O)=[CH:40][N:41]=2)=[CH:33][CH:32]=1)=[O:29])[CH3:26].CCN(CC)CC.[C:52]([NH2:61])([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)([CH3:54])[CH3:53]>CN(C=O)C.O>[CH2:25]([NH:27][C:28]([NH:30][C:31]1[N:36]=[CH:35][C:34]([C:37]2[S:38][C:39]([C:42]([NH:61][C:52]([CH3:54])([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[CH3:53])=[O:44])=[CH:40][N:41]=2)=[CH:33][CH:32]=1)=[O:29])[CH3:26]HATU (0.078 mg, 0.225 mmol) was added to a solution of 2-(6-{[(ethylamino)carbonyl]amino}pyridin-3-yl)-1,3-thiazole-5-carboxylic acid (Example 17, 60 mg, 0.205 mmol), Et3N (84 μL, 0.41 mmol) and cumylamine (28 mg, 0.205 mmol) in 3 mL DMF. After stirring at room temperature for two hours, the mixture was diluted with water and extracted with EtOAc. The product precipitated during the workup and it was collected by filtration, washed with water and EtOAc and dried (20 mg). MS (ESP): 410 (M+H+) for C21H23N5O2S.
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