ClN1C=[C:6]([Cl:8])[N:5]=[CH:4][NH:3]1.C[CH2:10][N:11](C(C)C)C(C)C.[CH2:18]([N:25]1[C:33]2[C:28](=[CH:29][C:30]([NH2:34])=[CH:31][CH:32]=2)[CH:27]=[N:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCOCC>CN(C=O)C.CCOC(C)=O>[CH2:18]([N:25]1[C:33]2[C:28](=[CH:29][C:30]([NH:34][C:10]3[N:11]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=3)=[CH:31][CH:32]=2)[CH:27]=[N:26]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1To 2,4-dichloro-1,2,5-triazine (526.1 mg, 3.51 mmol) in DMF (15 mL) at 0° C. was added DIEA (0.733 mL, 4.21 mmol). The resulting yellow solution was stirred at 0° C. for 20 min and 1-benzyl-1H-indazol-5-ylamine (783.5 mg, 3.51 mmol) was added in one portion followed by 2×2.5 mL DMF flask rinses. The resulting mixture was stirred at 0° C. for 30 min, at RT for 4.5 h, then diluted with EtOAc. The organic layer was washed twice with water and once with brine. The aqueous layer and washings were extracted with EtOAc. The combined organics were dried, concentrated, and purified by chromatography (SiO2, elution with 1:1 EtOAc-hexanes) to give a slightly impure pinkish solid. Trituration with Et2O gave (1-benzyl-1H-indazol-5-yl)-(4-chloro-[1,3,5]triazin-2-yl)amine as a light pink solid: MS m/z=337 [M+H]+. Calc'd for C17H13ClN6: 336.09.
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