[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][NH:10][N:9]=2)=[CH:4][C:3]=1[CH2:13][NH2:14].C([C:22]1[NH:23][CH:24]=CN=1)(C1NC=CN=1)=O.CN.C1C[O:32]CC1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][NH:10][N:9]=2)=[CH:4][C:3]=1[CH2:13][NH:14][C:24]([NH:23][CH3:22])=[O:32]To a solution of 2-chloro-5-(1H-pyrazol-3-yl)benzenemethanamine (i.e. the product of Step C of Synthesis Example 4) (2.4 g, 11.6 mmol) in THF (12 mL) and dichloromethane (12 mL) at 10° C. was added carbonyl diimidazole (2.8 g, 17.3 mmol). The reaction mixture was stirred at ambient temperature for 30 minutes and then cooled to 0° C. A solution of methylamine in THF (2 M, 12.0 mL, 24 mmol) was added, and the reaction mixture was stirred at ambient temperature for 15 h. The reaction mixture was then diluted with dichloromethane, washed with water and brine, concentrated and purified by preparative TLC (2% methanol in chloroform as eluant) to provide the title product as a solid (1.0 g).
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