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| | 3-(6-Chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol hydrochloride Basic information |
| Product Name: | 3-(6-Chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol hydrochloride | | Synonyms: | (2R,3S/2S,3R)-3-(4-Chloro-5-fluoro-6-pyriMidinyl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-;(2R,3S/2S,3R)-3-(4-Chloro-5-fluoro-6-pyriMidinyl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol hydrochloride (for Voriconazole);3-(6-Chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol hydrochloride;(αR,βS)-rel-6-chloro-α-(2,4-difluorophenyl)-5-fluoro-β-Methyl-α-(1H-1,2,4-triazol-1-ylMethyl)-4-pyriMidineethanol Monohydrochloride;3-(6-CHLORO-5-FLUOROPYRIMIDIN-4-YL)-2,(2,4-DIFLUORO PHENYL)-1(1H-1,2,4-TRIAZOL-1-YL)BUTANE-2-OL HYDRO CHLORIDE;3-(6-Chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol hy;( 2R,3S/2S,3R )-3-(4-chloro-5-fluoro-6-pyriMidinyl)-2-(2,40difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol HCl;-1-(1H-1,2,4-triazol-1-yl) | | CAS: | 188416-20-8 | | MF: | C16H14Cl2F3N5O | | MW: | 420.22 | | EINECS: | | | Product Categories: | | | Mol File: | 188416-20-8.mol |  |
| | 3-(6-Chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol hydrochloride Chemical Properties |
| storage temp. | Sealed in dry,Store in freezer, under -20°C | | solubility | DMSO (Slightly), Methanol (Slightly) | | form | Solid | | color | White to Off-White | | Stability: | Hygroscopic |
| | 3-(6-Chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol hydrochloride Usage And Synthesis |
| Uses | 3-(6-Chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1 can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly used in laboratory research and development processes and chemical production processes. | | Synthesis | 
Under nitrogen atmosphere, 9.35 g of zinc powder and 0.47 g of lead are introducedto 53 mL of dry tetrahydrofuran (THF) and the mixture is agitated for 3 hours under reflux. The reaction mixture is cooled to 25C and agitated continuously for 16 hours. In a separate container, 7.42 g of iodine is dissolved into 21 mL of dry tetrahydrofuran (THF) and the resultant solution is added dropwise to the reaction mixture over 80 minutes. Next, the reaction mixture is warmed to 45C and then cooled to 0C.[119] At room temperature, 6.53 g of 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone and 7.01 g of 6-(1-bromo ethyl)-4-chloro-5-fluoropyrimidine are dissolved into 53 mL of tetrahydrofuran (THF) and the resultant solution is added dropwise gradually to the reaction mixture, while maintaining the reaction temperature at 5C or lower. The reaction mixture is warmed to 25C and 8.84 g of glacial acetic acid dissolved in 84 mL of purified water is added dropwise to the reaction mixture. The solid metal residueis removed by filtering, the solvent is distilled off under reduced pressure, and the reaction product is extracted twice with 84 mL of ethyl acetate (EA). The extract is washed with 3.22 g of disodium ethylenediamine tetraacetate dihydrate dissolved in 161 mL of purified water, and further washed with 30 mL of saline. The organic layer is concentrated to a final volume of 56 mL, and a solution containing 1.2 g of hydrochloric acid in 6 mL of isopropanol is added dropwise thereto at 25C. The resultant crystals are filtered, washed with 5 mL of EA, and dried under reduced pressure for 12 hours at 50C to obtain 5.99 g of the target compound (yield 48.7%, purity 96.2%, HPLC, detected at a wavelength of 256 nm, 18C 4.6 X 250 mm, mobile phase 60% ACN, flow rate 1 mL/min).[120] 1H-NMR (200MHz, DMSO-d6) | (ppm) : 8.85(1H), 8.731H), 7.93(1H), 7.28~7.16(2H), 6.95~6.89(1H), 5.83(1H), 4.81(1H), 4.54(1H), 3.92(1H), 1.13(3H). | | References | [1] Patent: WO2011/96697, 2011, A2. Location in patent: Page/Page column 15-16
[2] Patent: US2014/350252, 2014, A1. Location in patent: Paragraph 0038; 0039; 0040
[3] Patent: CN105503834, 2016, A. Location in patent: Paragraph 0055; 0056 |
| | 3-(6-Chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol hydrochloride Preparation Products And Raw materials |
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