CAS: 1191237-80-5; (3Ar,4R,6R,6Ar)-4-(4-Aminopyrrolo[2,1-F][1,2,4]Triazin-7-yl)-6-(Hydroxymethyl)-2,2-Dimethyltetrahydrofuro[3,4-D][1,3]Dioxole-4-Carbonitrile

该化合物是一种结构特征杂质,与抗病毒药物Remdesivir的合成和降解有关,这种杂质出现在丙烯酸保护步骤或具体储存条件下,其识别和量化对于确保Remdesivir配方的纯度和功效至关重要.通常使用HPLC和LC-MS等分析方法来检测.适当控制这种杂质对于药品开发满足法规合规和维护产品安全至关重要.其定义明确的化学特性有利于方法验证和稳定研究,支持抗病毒药物制造的严格质量控制.

英文名称(3Ar,4R,6R,6Ar)-4-(4-Aminopyrrolo[2,1-F][1,2,4]Triazin-7-yl)-6-(Hydroxymethyl)-2,2-Dimethyltetrahydrofuro[3,4-D][1,3]Dioxole-4-Carbonitrile
中文名称瑞德西韦5号中间体
IUPAC名称(3aR,4R,6R,6aR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile
其它别名2-C-(4-Aminopyrrolo[2,1-F][1,2,4]Triazin-7-yl)-2,5-Anhydro-3,4-O-(1-Methylethylide-D-Altrononitrile; 2-C-(4-Aminopyrrolo[2,1-F][1,2,4]Triazin-7-yl)-2,5-Anhydro-3,4-O-(1-Methylethylidene)-D-Altrononitrile; D-Altrononitrile, 2-C-(4-Aminopyrrolo[2,1-F][1,2,4]Triazin-7-yl)-2,5-Anhydro-3,4-O-(1-Methylethylide; (3Ar,4R,6R,6Ar)-4-(4-Aminopyrrolo[1,2-F][1,2,4]Triazin-7-yl)-6-(Hydroxymethyl)-2,2-Dimethyl-Tetrahydrofuro[3,4-D][1,3]Dioxole-4-Carbonitrile; (4R)-4-(4-Aminopyrrolo[2,1-F][1,2,4]Triazin-7-yl)-6-(Hydroxymethyl)-2,2-Dimethyltetrahydrofuro[3,4-D][1,3]Dioxole-4-Carbonitrile; Remdesivir Impurity 7; Remdesivir N-2; Gs-5
CAS编号1191237-80-5
MFCD编号:MFCD32693253
分子式:C15H17N5O4分子量:331.33
产品CID: 253982
同类组份化合物CAS1911579-00-4 (tosylate)1191237-80-5 (free base)
产品分类有机原料 → 有机杂环化合物 → 吡咯并三嗪类

相似结构搜索
InChIKey: IJCOKJGMVJGKBB-CGEWXTDFSA-N
InChI=1S/C15H17N5O4/c1-14(2)23-11-9(5-21)22-15(6-16,12(11)24-14)10-4-3-8-13(17)18-7-19-20(8)10/h3-4,7,9,11-12,21H,5H2,1-2H3,(H2,17,18,19)/t9-,11-,12-,15+/m1/s1
计算化学: 氢键受体数8.0氢键供体数2.0可旋转键数2.0

物理性质

密度1.66±0.1 g/cm3(预测)
pKa:14.14±0.10(预测)
LogP:-1
溶解性DMSO:55.5(Max Conc. mg/mL);167.51(Max Conc. Mm) Ethanol:5.0(Max Conc. mg/mL);15.09(Max Conc. Mm) Pbs (Ph 7.2):0.3(Max Conc. mg/mL);0.91(Max Conc. Mm) DMF:12.0(Max Conc. mg/mL);36.22(Max Conc. Mm)
外观形态类白色至淡黄色固体
储存条件2-8°C,干燥,密封.
产品应用该化合物用于REMDESIVIR的研发和化学生产.

MSDS等安全信息

GHS符号GHS07
警示词Warning
危险描述H302-H315-H319-H335
防范说明P261-P280-P301+P312-P302+P352-P305+P351+P338
安全声明H303+H313+H333

上下游产品

瑞德西韦相关化合物5 (2R,3R,4R,5R)-2-(4-Aminopyrrolo[2,1-F][1,2,4]Triazin-7-yl)-3,4-Bis(Benzyloxy)-5-((Benzyloxy)Methyl)Tetrahydrofuran-2-Carbonitrile 1355357-49-1
(3R,4R,5R)-2-(4-Aminopyrrolo[2,1-F][1,2,4]Triazin-7-yl)-3,4-Bis(Benzyloxy)-5-((Benzyloxy)Methyl)Tetrahydrofuran-2-Carbonitrile 1191237-68-9
瑞德西韦母核 Gs-441524 1191237-69-0
瑞德西韦杂质1 (3R,4R,5R)-2-(4-Aminopyrrolo[2,1-F][1,2,4]Triazin-7-yl)-3,4-Bis(Benzyloxy)-5-((Benzyloxy)Methyl)Tetrahydrofuran-2-Ol 1355049-94-3
(2S,3R,4R,5R)-2-(4-Aminopyrrolo[2,1-F][1,2,4]Triazin-7-yl)-3,4-Bis(Benzyloxy)-5-((Benzyloxy)Methyl)Tetrahydrofuran-2-Ol

合成工艺路线路线简述

合成目标产物 Remdesivir N-2 主要起始原料 Gs-441524 And 2,2-Dimethoxypropane
(文献来源)合成步骤主要原料 Gs-441524 和 2,2-Dimethoxypropane

📜瑞德西韦母核置于potassium Carbonate体系中,用水,乙酸乙酯,丙酮用作溶剂,化学反应 0.5H,反应生成瑞德西韦5号中间体
参考文献: Methods For Treating Filoviridae Virus Infections[fr] Méthodes Pour Le Traitement D'Infections Virales à Filoviridae
标题: Methods For Treating Filoviridae Virus Infections[fr] Méthodes Pour Le Traitement D'Infections Virales à Filoviridae
摘要:提供了一种通过给予公式(iv)中的核糖苷,核糖苷磷酸盐及其前药来治疗filoviridae病毒感染的化合物,方法和药物组合物.所提供的化合物,组合物和方法特别适用于治疗马尔堡病毒,埃博拉病毒和库埃瓦病毒感染.

海关参考信息

2905122000-异丙醇
2905310000-1,2-乙二醇
2905320000-1,2-丙二醇
2905399001-1,3-丙二醇
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-11655255-B2
优先权日:2022-10-17
标题 :Method for catalytic asymmetric synthesis of phosphorus-stereogenic (P-stereogenic) nucleoside derivative and catalyst used therein
发明人：ZHANG WANBIN; WANG MO; ZHANG LU; HUO XIAOHONG; ZHANG ZHENFENG; YUAN QIANJIA; CHEN JIANZHONG
权利人:SPH NO 1 BIOCHEMICAL & PHARMACEUTICAL CO LTD; UNIV SHANGHAI JIAOTONG
摘要:A method for catalytic asymmetric synthesis of a phosphorus-stereogenic (P-stereogenic) nucleoside derivative of formula (3) and a catalyst used therein. The P-stereogenic nucleoside derivative (3) can be hydrolyzed to obtain remdesivir. Specifically, a nucleoside and phosphoryl chloride are subjected to asymmetric reaction under the catalysis of a chiral bicyclic imidazole catalyst in the presence of a base to produce the P-stereogenic nucleoside derivative of formula (3)

专利号:US-11612614-B2
优先权日:2020-10-20
标题:Isomorphs of Remdesivir and methods for synthesis of same
发明人：TRIPATHI VINAY SHANKAR; PATEL AKSHAY NIKHIL
权利人:ANZALP PHARMASOLUTIONS PVT LTD
摘要:A new isoform of 2-ethylbutyl (2S)-2-[[[(2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3/4-dihydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate (Remdesivir) having increased water solubility is disclosed, along with methods for making the same. Also disclosed are solid and liquid pharmaceutical compositions suitable for treating viral infections such as Arenaviridae, Coronaviridae, Filoviridae, Flaviviridae, or Paramyxoviridae viral infections which contain an effective amount of Remdesivir prepared according to the inventive method and the use of those compositions for treating such viral infections.

专利号:US-2021228605-A1
优先权日:2020-10-20
标题:Isomorphs of remdesivir and methods for synthesis of same

专利号:US-2021161927-A1
优先权日:2020-10-20
标题:Isomorphs of remdesivir and methods for synthesis of same

其他信息查阅

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品牌试剂参考报价(招募中)

实用工具

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✅ COA系统入驻 | 共享模式

主要参考文献

1. Siegel D, Hui HC, Doerffler E, Clarke MO, Chun K, Zhang L, Neville S, Carra E, Lew W, Ross B, Wang Q, Wolfe L, Jordan R, Soloveva V, Knox J, Perry J, Perron M, Stray KM, Barauskas O, Feng JY, Xu Y, Lee G, Rheingold AL, Ray AS, Bannister R, Strickley R, Swaminathan S, Lee WA, Bavari S, Cihlar T, Lo MK, Warren TK, Mackman RL. Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses. J Med Chem. 2017 Mar 9;60(5):1648-1661. doi: 10.1021/acs.jmedchem.6b01594. Epub 2017 Feb 14. 30(3):269-271. doi: 10.1038/s41422-020-0282-0. Epub 2020 Feb 4.