[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][O:9]2)=[CH:4][C:3]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13].[CH:16]([C:19]1[C:27]2[C:22](=[CH:23][C:24]([O:28][CH2:29][CH2:30][NH2:31])=[CH:25][CH:26]=2)[NH:21][N:20]=1)([CH3:18])[CH3:17].CC(O)C.C(C1C2C(=CC(OCCN)=CC=2)NN=1)(C)C>CC(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([OH:9])[CH2:10][NH:31][CH2:30][CH2:29][O:28][C:24]2[CH:23]=[C:22]3[C:27]([C:19]([CH:16]([CH3:18])[CH3:17])=[N:20][NH:21]3)=[CH:26][CH:25]=2)=[CH:4][C:3]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13].[ClH:1]2-Propanol (1.5 mL) was added to (R)-N-(2-chloro-5-(oxiran-2-yl)phenyl)methanesulfonamide (28.6 mg) that can be produced by the method described in Reference Example 69 or the like, and a 2-(3-isopropylindazol-6-yloxy)ethanamine-2-propanol solution [37.5 μL; solution prepared by dissolving 2-(3-isopropylindazol-6-yloxy)ethanamine (306.4 mg) that can be produced by the method described in Reference Example 68 or the like, in 2-propanol (347.5 μL)]. The mixture was stirred overnight at reflux. The reaction solution was cooled to room temperature, and then nitrogen gas was blown into the reaction solution to evaporate the solvent. The resulting residue was purified by HPLC, and then the purification product was dissolved in water (1 mL) and a 1 mol/L aqueous solution of hydrochloric acid (150 μL; manufactured by Kanto Chemical Co., Inc.). The solution was freeze-dried, and thus the title compound was obtained in the form of hydrochloride (18.1 mg).
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