N1(O[C:11]2[N:16]=[C:15]([NH:17][CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])[CH2:20]3)[C:14]([C:35](=[O:37])[NH2:36])=[CH:13][N:12]=2)C2C=CC=CC=2N=N1.[NH2:38][C:39]1[CH:40]=[C:41]([CH:46]=[CH:47][CH:48]=1)[NH:42][C:43](=[O:45])[CH3:44].CC1C=CC(S(O)(=O)=O)=CC=1.O>O1CCOCC1.CCOC(C)=O>[C:43]([NH:42][C:41]1[CH:40]=[C:39]([NH:38][C:11]2[N:16]=[C:15]([NH:17][CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])[CH2:20]3)[C:14]([C:35](=[O:37])[NH2:36])=[CH:13][N:12]=2)[CH:48]=[CH:47][CH:46]=1)(=[O:45])[CH3:44]A mixture of benzyl 3-((2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-5-carbamoylpyrimidin-4-ylamino)methyl)piperidine-1-carboxylate (582 mg, 1.16 mmol), 3′-amino-acetanilide (210 mg, 1.40 mmol) and pTsOH (220 mg, 1.16 mmol) in dioxane (10 mL) was stirred at 100 C for 4 h. Water and EtOAc were added. The organic phase was separated, washed with 1N HCl. During the washing white solids precipitated out, which were collected to give the titled compound (412 mg). MS 518.5 (M+H); UV 201.6, 249.8 nm.
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