[ClH:1].CCCCCCC.[CH3:9][O:10][C:11]1[N:16]=[C:15](/[CH:17]=[CH:18]/[C:19]2[N:37]=[C:22]3[C@H:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]([F:36])([F:35])[F:34])[CH2:24][CH2:25][CH2:26][N:21]3[N:20]=2)[CH:14]=[CH:13][C:12]=1[N:38]1[CH:42]=[C:41]([CH3:43])[N:40]=[CH:39]1>CC(O)C>[ClH:1].[CH3:9][O:10][C:11]1[N:16]=[C:15](/[CH:17]=[CH:18]/[C:19]2[N:37]=[C:22]3[C@H:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]([F:36])([F:35])[F:34])[CH2:24][CH2:25][CH2:26][N:21]3[N:20]=2)[CH:14]=[CH:13][C:12]=1[N:38]1[CH:42]=[C:41]([CH3:43])[N:40]=[CH:39]1Concentrated hydrochloric acid (14.3 μL) and heptane (7 mL) were added to a solution of (8S)-2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-8-(2-trifluoromethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine (79.77 mg) in 2-propanol (3 mL). A small amount of the crystals obtained in Example 5 were added as seed crystals with stirring at room temperature. The mixture was transferred to a low temperature laboratory at about 5° C. and stirred for one hour. Thereafter, 1 mL of heptane was further added, followed by stirring for several minutes. When the precipitated solid was collected by filtration through a glass filter, the solid was precipitated in the filtrate. The precipitated solid was collected by filtration through a glass filter and dried under reduced pressure at room temperature to obtain 38.02 mg of the title compound as white solid crystals.
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