C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:13]([O:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([O:31][CH2:32][CH3:33])[C:24]=1[C:25]1[CH:26]=[N:27][N:28]([CH3:30])[CH:29]=1)[C:19](O)=[O:20])[CH3:14].Cl.Cl.[O:36]=[C:37]1[C:51]2[C:46](=[CH:47][CH:48]=[C:49]([C:52]3[CH:53]=[C:54]([C:58]([OH:60])=[O:59])[CH:55]=[N:56][CH:57]=3)[CH:50]=2)[O:45][C:39]2([CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH2:38]1.Cl>O.C(N(CC)CC)C.CN(C=O)C>[CH2:13]([O:15][C:16]1[CH:17]=[C:18]([C:19]([N:42]2[CH2:41][CH2:40][C:39]3([CH2:38][C:37](=[O:36])[C:51]4[C:46](=[CH:47][CH:48]=[C:49]([C:52]5[CH:53]=[C:54]([C:58]([OH:60])=[O:59])[CH:55]=[N:56][CH:57]=5)[CH:50]=4)[O:45]3)[CH2:44][CH2:43]2)=[O:20])[CH:22]=[C:23]([O:31][CH2:32][CH3:33])[C:24]=1[C:25]1[CH:26]=[N:27][N:28]([CH3:30])[CH:29]=1)[CH3:14]Carbonyldiimidazole (130 mg) and triethylamine (0.446 mL) were added to a DMF solution (4 mL) of 3,5-diethoxy-4-(1-methyl-1H-pyrazol-4-yl)benzoic acid (232 mg), and stirred at 70° C. for 2 hours. To the reaction liquid, added was a DMF suspension (2 ml) of 5-(4-oxospiro[chroman-2,4′-piperidin]-6-yl)pyridine-3-carboxylic acid dihydrochloride (370 mg) and triethylamine (0.335 ml) that had been prepared separately, and further stirred at that temperature for 1 hour. 1 N hydrochloric acid and water were added to the reaction liquid, the resulting solid was taken out through filtration, and recrystallized from methanol to obtain the title compound.
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