CCN(C(C)C)C(C)C.[CH3:10][C:11]1[C:16]([NH:17][C:18]2[N:23]=[C:22]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[CH:21]=[CH:20][N:19]=2)=[CH:15][C:14]([NH2:30])=[CH:13][N:12]=1.[CH2:31]([N:33]1[CH2:38][CH2:37][N:36]([CH2:39][C:40]2[CH:48]=[CH:47][C:43]([C:44](O)=[O:45])=[CH:42][CH:41]=2)[CH2:35][CH2:34]1)[CH3:32].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[CH2:31]([N:33]1[CH2:38][CH2:37][N:36]([CH2:39][C:40]2[CH:41]=[CH:42][C:43]([C:44]([NH:30][C:14]3[CH:13]=[N:12][C:11]([CH3:10])=[C:16]([NH:17][C:18]4[N:23]=[C:22]([C:24]5[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=5)[CH:21]=[CH:20][N:19]=4)[CH:15]=3)=[O:45])=[CH:47][CH:48]=2)[CH2:35][CH2:34]1)[CH3:32]DIEA (47 μL, 0.27 mmol) was added into a solution of 2-Methyl-N3-(4-pyridin-3-yl-pyrimidin-2-yl)-pyridine-3,5-diamine (15 mg, 0.054 mmol), 4-((4-ethylpiperazin-1-yl)methyl)benzoic acid (16.1 mg, 0.61 mmol), BOP (33.4 mg, 0.76 mmol) in DMF (1.5 mL). The reaction mixture is stirred at rt under argon atmosphere overnight. The reaction mixture was then purified by Waters semi-preparative HPLC to the final product. MS (ESI+) m/z 509.1 [M+H]+.
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