Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 29274-24-6, name is 5-Chloropyrazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H4ClN3
To benzyl (7S)-7-methyl-5-(2-(2H-1,2,3-triazol-2-yl)benzoyl)-1,2,5-oxadiazepane-2-carboxylate (4.4 g) obtained in Step A of Example 2 was added 5.1M hydrogen bromide acetic acid solution (30 mL), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, to a solution of the residue in 2-propanol (40 mL) was added 4-chloro-2,6-dimethylpyrimidine (2.23 g), and the mixture was stirred at 70 C. for 10 hr. The reaction mixture was cooled to 0 C., saturated aqueous sodium hydrogencarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate), and crystallized (heptane/ethyl acetate) to give the title compound (2.30 g). 1H NMR (300 MHz, DMSO-d6) delta 1.02-1.50 (3H, m), 2.16-2.46 (6H, m), 2.95-3.29 (1H, m), 3.40-3.75 (3H, m), 3.79-4.74 (3H, m), 6.31-6.77 (1H, m), 7.05-8.30 (6H, m). MS: [M+H]+ 394.1. d value (or d-spacing) of specific peak in powder X-ray diffraction pattern=15.5, 7.9, 7.7, 7.4, 6.5, 5.6, 5.1, 4.3, 4.0, 3.67, 3.62, 3.57, 3.52 A. The title compound (11.4 mg) was obtained using ((7S)-7-methyl-1 ,2,5-oxadiazepan-5-yl)(2-(2H- 1 ,2,3-tri- azol-2-yl)phenyl)methanone hydrobromide (60 mg) obtained in Step A of Example 92 and 5-chloropyrazolo[1, 5-a]pyrimidine (26.1 mg) obtained in Reference Example 24 in the same manner as in Step B of Example 2. MS: [M+H]+405.1.
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Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAMEI, Taku; ARIKAWA, Yasuyoshi; OHASHI, Tomohiro; IMAEDA, Toshihiro; FUJIMORI, Ikuo; MIKI, Takashi; YONEMORI, Jinichi; OGURO, Yuya; SUGIMOTO, Takahiro; SETO, Masaki; NISHIDA, Goushi; KAMATA, Makoto; IMOTO, Hiroshi; (132 pag.)US2018/155333; (2018); A1;,
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