Category: 864448-41-9

Application of 864448-41-9, These common heterocyclic compound, 864448-41-9, name is tert-Butyl 3-oxa-7,9-diazabicyclo[3.3.1]nonane-7-carboxylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution tert-butyl 3-oxa-7,9-diazabicyclo[3.3.1]nonane-7-carboxylate (400mg, L75 mmol) and Et3N (0.49 niL, 3.5 mrnol) in DCM (10 mL) was added CbzCl (448 mg, 2.63 mmoi) at room temperature. The reaction mixture was stirred at room temperature for 2 hours and then water (10.0 mL) was added, and the mixture is extracted three times with EtOAc (30 rnL each). The combined organic phase was dried over Na2SO4 and concentrated. The residue was purifiedby silica gel colunm chromatography (PE: EtOAc, from 10:1 to 2: 1) to give a white solid (300 mg). The solid was dissolved in ACN (8 mL) and water (2 rnL), to which were added RuC13 (35 mg, 0.170 mmol) and Na104 (532 mg, 2.48 mmoi). The reaction mixture was stirred at room temperature for 36 hours and water (10 niL) was added, and the mixture was extracted three times with EtOAc (20 mL), The combined organic phase was dried over Na2SO4 andconcentrated. The residue was purified by column (PE: EtOAc, from 10:1 to 1: 1) to give the desired product 13a as a yellow oil (150 mg). LCMS (M-100+H) 277.1

The synthetic route of 864448-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HU, Taishan; KOU, Buyu; LIU, Haixia; ZHANG, Zhisen; ZHOU, Zheng; (54 pag.)WO2018/11162; (2018); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 864448-41-9 as follows. Formula: C11H20N2O3

To a mixture of 3-oxa-7,9-diaza-bicyclo[3.3.1]nonane-7-carboxylic acid tert-butyl ester (171 mg, 0.75mmol) and DIPEA(0.45 mL, 2.5 mmol) in CH2C12 (10 mL) was added (R)-6- bromomethyl-4-(2-chloro-4-fluoro-phenyl)-2-thiazol-2-yl-l,4-dihydro-pyrimidine-5-carboxylic acid methyl ester(222 mg, 0.5 mmol). The mixture was stirred at room temperature for 16 hours The mixture was concentrated in vacuo. The residue was purified by flash column chromatography to afford 9-[(R)-6-(2-chloro-4-fluoro-phenyl)-5-methoxycarbonyl-2-thiazol-2- yl-3,6-dihydro-pyrimidin-4-ylmethyl]-3-oxa-7,9-diaza-bicyclo[3.3.1]nonane-7-carboxylic acid tert-butyl ester as yellow oil (0.28 g, 94%). MS: calc’d (MH+) 592, measured (MH+) 592.

According to the analysis of related databases, 864448-41-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GUO, Lei; HU, Taishan; HU, Yimin; KOCER, Buelent; KOU, Buyu; LI, Gangqin; LIN, Xianfeng; LIU, Haixia; SHEN, Hong; SHI, Houguang; WU, Guolong; ZHANG, Zhisen; ZHOU, Mingwei; ZHU, Wei; WO2014/184328; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics