[Br:1][C:2]1[CH:3]=[N:4][N:5]2[C:10]([OH:11])=[C:9]([C:12]([OH:14])=O)[CH:8]=[N:7][C:6]=12.[C:15]1([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.C(OCC)(=O)C.Cl>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][N:5]2[C:10]([OH:11])=[C:9]([C:12]([N:24]3[CH2:25][CH2:26][CH:21]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:22][CH2:23]3)=[O:14])[CH:8]=[N:7][C:6]=123-Bromo-7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylic acid (6.3 g, 24.5 mmol) obtained in step 1 and 4-phenylpiperidine (7.9 g, 49.0 mmol) were suspended in methylene chloride (120 mL), triethylamine (13.7 ml, 98.1 mmol) and 50% 1-propylphosphonic acid anhydride cyclic trimer-ethyl acetate solution (6.0 g, 49.0 mmol) were added at 0° C., and the mixture was stirred at 0° C. for 2 hr. 4-Phenylpiperidine (7.9 g, 49.0 mmol), triethylamine (13.7 mL, 98.1 mmol) and 50% 1-propylphosphonic acid anhydride cyclic trimer-ethyl acetate solution (6.0 g, 49.0 mmol) were added to the reaction mixture, and the mixture was further stirred at 0° C. for 2 hr. 2 mol/L Hydrochloric acid (100 mL) was added to the reaction mixture, the organic layer and the aqueous layer were separated, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. 2 mol/L Hydrochloric acid (100 mL) was added to the residue, and the mixture was stirred at 30° C. for 2 hr. The precipitate was collected by filtration, and washed with water (100 mL) to give the title compound (7.7 g, 78%).
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