1355049-94-3Relevant articles and documents
Continuous Flow C-Glycosylation via Metal-Halogen Exchange: Process Understanding and Improvements toward Efficient Manufacturing of Remdesivir
Kappe, C. Oliver,Von Keutz, Timo,Williams, Jason D.
, p. 2362 - 2368 (2020)
As remdesivir is the first approved treatment for COVID-19 (SARS-CoV-2), its production is likely to be of vital importance in the near future. Continuous flow processing has been demonstrated as a key technology in the manufacturing of high-volume active pharmaceutical ingredients and is considered for use in this synthetic sequence. In particular, the challenging C-glycosylation of a pyrrolotriazinamine via metal-halogen exchange was identified as a transformation with significant potential benefit, as exemplified by calorimetric analysis of each reaction step. Multiple simplifications of this process were attempted in batch but in general were found to be unfruitful. The five-feed process was then transferred to a flow setup, where specific conditions were found to circumvent solid formation and permit stable processing. Detailed optimization of stoichiometries provided an improvement upon batch conditions with a total residence time of 1 min.
Development of a Large-Scale Cyanation Process Using Continuous Flow Chemistry en Route to the Synthesis of Remdesivir
Badalov, Pavel,Chtchemelinine, Andrei,Gao, Detian,Heumann, Lars,Stevens, Andrew C.,Vieira, Tiago
, p. 2113 - 2121 (2020)
The implementation of cyanation chemistry at manufacturing scales using batch equipment can be challenging because of the hazardous nature of the reagents employed and the tight control of reaction parameters, including cryogenic temperatures, that help t
Intermediate of and preparation method thereof
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Paragraph 0348-0346, (2021/09/08)
The present invention provides an intermediate of Remdesivir and a preparation method therefor. The preparation method has the advantages of low costs, high yield, good product purity, etc. , and can achieve the efficient synthesis of Remdesivir. In each formula, R1, R2, R3, R4, R5, R8, PG and X are as defined in the description.
Preparation method of ridecevir intermediate
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Paragraph 0029; 0033-0034; 0039-0040, (2021/06/02)
The invention discloses a preparation method of a ridecevir intermediate. The preparation method comprises the following steps: firstly, reacting 7-iodopyrrolo [2, 1-f] [1, 2, 4] triazine 4-amine with N, N-dimethylformamide dimethyl acetal, then adding i-PrMgCl or butyl lithium into the product obtained in the previous step for reacting, then adding 2, 3, 5-tribenzyloxy-D-ribonucleic acid 1, 4-lactone, and finally removing a protecting group to obtain the remdesivir intermediate 1-C-(4-aminopyrrole [2, 1-f] [1, 2, 4] triazine-7-yl)-2, 3, 5-trioxy-(benzyl)-D-ribose furanose. According to the preparation method of the ridecevir intermediate, a mature product in the current market is selected as a reactant, the raw materials are easy to obtain, and the production cost is reduced; and the method has the advantages of simple process, short time consumption, high production efficiency, high yield, mild reaction conditions and simple and convenient post-treatment, is suitable for large-scale preparation, and has great application prospects.