Acetic Acid → HCID 10431406, 화합물

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[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][C:11]([C:20]([N:22]3[CH2:27][CH:26]([CH3:28])[NH:25][CH:24]([CH3:29])[CH2:23]3)=[O:21])=[N:10]2)=[CH:5][CH:4]=1.C=O.[C:32](O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:12][C:11]([C:20]([N:22]3[CH2:27][CH:26]([CH3:28])[N:25]([CH3:32])[CH:24]([CH3:29])[CH2:23]3)=[O:21])=[N:10]2)=[CH:5][CH:4]=1

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실험 절차

4-[1-(6-Methoxy-3-pyridyl)-5-phenylpyrazole-3-carbonyl]-2,6-dimethylpiperazine (29.7 mg) obtained in Example 22 was dissolved in ethanol (2.0 mL). To the solution, 35% aqueous formalin solution (0.0325 mL), acetic acid (0.0217 mL), and sodium cyanoborohydride (9.2 mg) were added at room temperature, followed by stirring for 1.5 hours. The reaction mixture was partitioned between aqueous sodium hydrogencarbonate and chloroform at 0° C. The aqueous layer was further extracted with chloroform. The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate anhydrate. After filtration, the solvent was removed under reduced pressure, and the residue was brought to dryness, to thereby give the title compound (40 mg, quantitative amount).