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Ethanol, 2-[[(3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylthio)-4-pyrimidinyl]amino]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]is a complex organic compound with a unique molecular structure. It is characterized by its chiral centers and functional groups, which contribute to its specific properties and reactivity. This ethanol derivative is known for its role in the synthesis of pharmaceutical compounds, particularly as a reagent in the production of Ticagrelor (T437700) derivatives.

376608-74-1

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376608-74-1 Usage

Uses

Used in Pharmaceutical Industry:
Ethanol, 2-[[(3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylthio)-4-pyrimidinyl]amino]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]is used as a reagent in the synthesis of Ticagrelor (T437700) derivatives. Ticagrelor is an antiplatelet agent that helps prevent blood clots and is used to treat patients with acute coronary syndrome or a history of myocardial infarction, stroke, or peripheral arterial disease. The unique structure of this ethanol derivative allows it to participate in the formation of these important therapeutic agents, contributing to their efficacy and safety in treating cardiovascular conditions.

Check Digit Verification of cas no

The CAS Registry Mumber 376608-74-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,7,6,6,0 and 8 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 376608-74:
(8*3)+(7*7)+(6*6)+(5*6)+(4*0)+(3*8)+(2*7)+(1*4)=181
181 % 10 = 1
So 376608-74-1 is a valid CAS Registry Number.

376608-74-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-[[(3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylthio)-4-pyrimidinyl]amino]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-ethanol

1.2 Other means of identification

Product number -
Other names Ticagrelor intermediate 12

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:376608-74-1 SDS

376608-74-1Relevant academic research and scientific papers

Synthesis and biological evaluation of: N 6derivatives of 8-azapurine as novel antiplatelet agents

Tian, Nana,Wang, Juan,Wang, Yeming,Yan, Hong,Zhao, Zhichang

, p. 1414 - 1427 (2021/11/09)

Two series of novel N6 derivatives of 8-azapurine I and II were designed as antiplatelet agents. Series I and II were N6 amino derivatives and N6 hydrazone derivatives of 8-azapurine, respectively. The compounds were synthesized in acceptable yields via conventional procedures, including nucleophilic substitution, diazotization, and amination or hydrazonation with amino alcohol and 4,6-dichloropyrimidine as starting materials. To assess the ability of the synthesized compounds as antiplatelet agents, the ADP-induced platelet aggregation assay of Born was performed both in vitro and in vivo using ticagrelor as a reference control substance. The analysis of the structure-activity relationship and molecular docking were also discussed in detail. The results demonstrated that series I and II compounds exhibited antiplatelet activity in vitro and IIh was the most active compound (IC50 = 0.20 μM) among the target compounds, being almost 4-fold better than ticagrelor (IC50 = 0.74 μM). For a preliminary assessment of the safety profile, a bleeding test (mouse tail) and a single-dose toxicity test were conducted. The use of compound IIh resulted in a shorter bleeding time, less blood loss and lower acute toxicity compared to ticagrelor. In addition, a molecular docking study was performed to investigate the binding capacity and binding mode between IIh and P2Y12. This journal is

NEW USE OF TRIAZOLO[4,5-D]PYRIMIDINE DERIVATIVES

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Page/Page column 13; 15, (2021/01/29)

Triazolo[4,5-d]pyrimidine derivatives of formula (I) for use in prognosis and/or diagnosis of bacterial infection in a host mammal and method of imaging thereof. Formula (I) wherein R1 is C3-5 alkyl optionally substituted by one or m

Preparation process of ticagrelor intermediate

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Paragraph 0014; 0026-0028, (2020/12/09)

The invention discloses a preparation process of a ticagrelor intermediate. The process comprises the following steps of dissolving 4,6-dichloro-2-(propylthio)-5-aminopyrimidine and sodium bicarbonatein water at a temperature of 15-25 DEG C; performing heating, adding an aqueous solution of 2-[[(3aR, 4S, 6R, 6aS)-6-amino-2, 2-dimethyltetrahydro-3aH- cyclopentadiene [d] [1,3]-dioxol-4-yl] oxy]-1-ethanol (III) or a salt thereof, and performing stirring at a constant temperature until a reaction is finished; stopping heating, cooling a reaction mixture, adding ethyl acetate, separating liquid, and washing an organic phase with water; stirring the organic phase, slowly dropwise adding n-hexane at a certain temperature, and separating out a solid to obtain the intermediate. According to the process, the use of excessive organic base such as triethylamine is avoided, the cheap and easily available sodium bicarbonate is used, the production cost is low, the reaction time is short, three wastes are few, and the obtained ticagrelor intermediate is the solid with the high purity, is high in yield and is more suitable for industrial production.

Synthesis of ticagrelor analogues belonging to 1,2,3-triazolo[4,5-d]pyrimidines and study of their antiplatelet and antibacterial activity

Goffin, Eric,Jacques, Nicolas,Lancellotti, Patrizio,Musumeci, Lucia,Nchimi, Alain,Pirotte, Bernard,Oury, Cécile

, (2020/09/11)

Based on the recent observation that the antiplatelet agent ticagrelor and one of its metabolite exert bactericidal activity against gram-positive bacteria, a series of 1,2,3-triazolo[4,5-d]pyrimidines structurally related to ticagrelor were synthesized and examined as putative antiplatelet and antibacterial agents. The aim was to assess the possibility of dissociating the two biological properties and to find novel 1,2,3-triazolo[4,5-d]pyrimidines expressing antiplatelet activity and devoid of in vitro antibacterial activity. The new compounds synthesized were known metabolites of ticagrelor as well as structurally simplified analogues. Some of them were found to express antiplatelet activity and to lose the antibacterial activity, supporting the view that the two activities were not necessarily linked.

Production process of ticagrelor fine product

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Paragraph 0020-0022; 0027-0029; 0034-0036, (2020/12/09)

The present invention discloses a production process of a ticagrelor fine product. The process comprises the steps of adopting 4,6-dichloro-5-amino-2-propylthiopyrimidine (IIa) and a compound (IIb) asstarting raw materials, and carrying out five processes including a substitution process I, a cyclization process, a substitution process II, a hydrolysis process and a refining process to finally obtain the ticagrelor fine product. The method provides a ticagrelor production process, uses cheap and easily available raw materials, has the advantages of low production cost, simple reaction conditions, convenient post-treatment, high yield and high product purity, and is more suitable for industrial production.

Improved preparation method of ticagrelor intermediate (by machine translation)

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Paragraph 0037-0048, (2020/03/17)

Step, Step: Reaction 1: Reaction of Compound 1 and Compound 2 with ethylene glycol, triethylamine under nitrogen protection, to obtain ticagrelor intermediate product, wherein the mixed solvent is an alcohol solvent, weak alkaline agent, in which the purity of intermediate product, is not less than, and the content of impurities, is not more than, in step (II) of inert gas protection descent temperature; to obtain ticagrelor intermediate. 2: The mixed solvent is obtained by filtering, organic layers under reduced pressure . The product obtained in Step 1, is obtained by adding an inert solvent (II), (II) and purifying/water, to, obtain a (II) ticagrelor intermediate product, obtained 99.2%, by stirring and dissolving, 3 into 0.05%; an active carbon decolorizing, filtrate .] 99.2%, filtering method of an 3 intermediate product thereof, 0.05%. is carried out in an inert gas protection falling temperature. (by machine translation)

A cyclopentyl pyrimidine compounds of the solvent-free preparation method

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Paragraph 0022-0031, (2018/11/22)

The invention relates to a solvent-free preparation method of a cyclopentyl pyrimidine compound and belongs to the field of a chemical preparation method. According to the solvent-free preparation method of the cyclopentyl pyrimidine compound (SM-C), SM-A is reacted with SM-B without a solvent under an alkaline condition to generate the SM-C. According to the method provided by the invention, an organic solvent is not used so that the production cost is reduced, the environmental pollution is reduced, the post-treatment is simplified and removal of organic solvent is not needed; a solvent-free reaction is carried out so that the reaction volume is greatly reduced and the production capability of equipment is improved; the solvent-free reaction is carried out so that the reaction concentration is improved, the conversion rate of raw materials of the reaction is improved, the reaction speed is improved and the reaction time is greatly shortened; meanwhile, the reaction can produce under a normal-pressure condition and a high-pressure reaction kettle is not needed so that the production is facilitated.

Conformational analysis of ticagrelor: effect of noncovalent interaction on conformational population

Fan, Qiangwen,Tan, Hongbo,Wang, Yeming,Song, Xiuqing,Yan, Hong

, p. 1663 - 1670 (2018/07/03)

In order to track the source of duplicated peaks in the 1H-NMR spectrum of Ticagrelor, variable-temperature NMR (VT-NMR) experiment was carried out with temperature increasing from 300 to 343?K. The result showed that the phenomenon was brought forth by coexistence of conformational isomers. Subsequently, conformational search was carried out by molecular mechanics (MM) stimulations associating with quantum mechanics (QM) calculations. The results revealed that the isomers resulting in duplicated proton peaks were introduced by the rotation of 2,4-diflurophenyl group on C3’position of cyclopropyl. Finally, noncovalent interaction (NCI) topological analysis of the conformers exhibited that CH-π interactions and H-bonds play important roles in controlling the population of conformers of ticagrelor.

An NMR and DFT investigation on the interconversion of 9-substituented-N 6-hydrazone-8-azaadenine derivatives: proton migration or conformational isomerization?

Fan, Qiangwen,Wang, Yeming,Yan, Hong

, p. 871 - 879 (2018/02/16)

A newly synthesized N6-arylhydrazone-8-azaadenine derivatives (1) showed significant differences in NMR spectra with previously synthesized analogues, specifically, the hydrogens of N1’H and C3’H in all the titled compounds showed two groups of signals in their 1H-NMR spectra. In order to investigate whether the duplication of proton signals were related to a mixture of conformational isomers which rotated around C-N1’ bond or configurational isomers which resulted from proton migration, variable temperature NMR and 2D-NOESY experiments were carried out in conjunction with density function theory (DFT) calculations at the B3LYP/6-311G (d,p)//B3LYP/6-31G (d,p) level. The results indicated that it was the conformational isomerism rather than hydrogen transfer that induced the reproduction of proton signals, which was attributed to lower barrier energy and larger rate constant of the former process.

Preparation method of ticagrelor

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Paragraph 0056-0060; 0065; 0066-0070, (2019/04/30)

The invention provides a preparation method of ticagrelor. According to the preparation method, a compound shown in a formula (i) is used as a raw material, and the ticagrelor is prepared by means ofcondensation, ring formation, condensation and deprotection; the preparation method is simple and convenient in technological process and easy to operate, thus being suitable for large-scale production; furthermore, the preparation method provided by the invention is mild in synthesis conditions, high in product yield and good in product purity, can effectively control the preparation cost, and reduces the medication burden of patients.

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