Route Design in the 21st Century: The ICSYNTH Software Tool as an Idea Generator for Synthesis Prediction

The new computer-aided synthesis design tool ICSYNTH has been evaluated by comparing its performance in predicting new ideas for route design to that of historical brainstorm results on a series of commercial pharmaceutical targets, as well as literature data. Examples of its output as an idea generator are described, and the conclusion is that it adds appreciable value to the performance of the professional drug research and development chemist team.

Anders Bøgevig ^‡, Hans-Jürgen Federsel ^*†,Fernando Huerta ^‡, Michael G. Hutchings ^*§, Hans Kraut ^§, Thomas Langer ^†, Peter Löw ^§, Christoph Oppawsky ^§, Tobias Rein ^‡, and Heinz Saller ^§

^† Chemical Development, AstraZeneca R&D, Silk Road Business Park, Macclesfield, SK10 2NA Cheshire, U.K.

^‡ Chemnotia AB, Forskargatan 20 J, 151 36 Södertälje,Sweden

^§ InfoChem GmbH, Landsberger Straße 408/V, D-81241 München, Germany

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/op500373e

Publication Date (Web): January 22, 2015

Copyright © 2015 American Chemical Society

*(H.-J.F.) E-mail: Hans-Jurgen.Federsel@astrazeneca.com., *(M.G.H.) E-mail:mghutchings@infochem.de.

http://pubs.acs.org/doi/full/10.1021/op500373e

Currently, ICSYNTH has assumed a place as a unique predictive tool for route design in Chemical Development in AZ. While it is finding valuable commercial application in our own and others’ hands, it remains a work in progress.

http://infochem.de/

InfoChem’s powerful synthesis planning tool now in Version 2.0. Read more …

InfoChem will be represented at the forthcoming ACS Meeting in San Diego. You will find Dr. Josef Eiblmaier, Dr. Valentina Eigner Pitto, and Dr. Peter Loew …

ICSYNTH

SEE…………….http://www.slideshare.net/Haxel/icic-2014-knowledgebased-de-novo-molecular-design-using-icsynth-frp

http://infochem.de/products/software/icsynth.shtml

http://infochem.de/content/downloads/icsynth.pdf

InfoChem’s ICSYNTH is a powerful computer aided synthesis design tool that enables chemists to generate synthetic pathways for a target molecule. The benefit is that ICSYNTH can facilitate innovation by stimulating ideas for alternative or novel synthetic routes that otherwise may not be considered. This may lead to improved route design, for example shorter pathways or more economical reaction modifications.

After inputting the target, users can select different synthetic strategies depending on requirements. ICSYNTH then automatically generates a multistep interactive synthesis tree – each node on the tree representing a precursor. The advantages are that the suggested reactions are based on, and linked to, published reactions (or their analogs) and the precursor availability is automatically checked in commercial catalogs. Users can modify the synthesis tree or select precursors for further analysis.

At the heart of ICSYNTH is an algorithmic chemical knowledge base of transform libraries that are automatically generated from reaction databases. The number of transform libraries is only limited by the availability of validated reaction databases.
In addition to retro synthesis design, ICSYNTH has a forward reaction prediction module that offers reactivity mapping for the target molecule.Version 2.0 of ICSYNTH was launched in April 2014. The completely re-designed user interface (based on JavaScript) and major improvements in the algorithm responsible of the precursor search are the main enhancements of Version 2.0. In addition the forward reaction prediction algorithm has been optimized. Click here to see a complete version history.

INFOCHEM GESELLSCHAFT FÜR CHEMISCHE INFORMATION MBH

Landsberger Straße 408/V
D-81241 München
Germany

PHONE:	+49 (0)89 58 30 02
FAX:	+49 (0)89 580 38 39
EMAIL:	info@infochem.de

Historische Bilder der Landsberger Straße – An der Trambahnhaltestelle Holzapfelstraße endet – Münchner Straßen – München – Süddeutsche.de

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Light-Controlled Release of Cyclodextrin

 

Light-Controlled Release of Cyclodextrin

Photoswitch reversibly releases cyclodextrin from molecular axle

The fabrication of photocontrolled molecular machines is one of the significant topics in supramolecular chemistry. To date, a great number of artificial molecular machines with promising photophysical properties, such as molecular shuttles and molecular switches, have shown potential applications in chemical and biological fields.
Read more
http://www.chemistryviews.org/details/ezine/7283451/Light-Controlled_Release_of_Cyclodextrin.html 




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Trapping Radicals to Make Acylpyrroles

Trapping Radicals to Make Acylpyrroles

 

Radical processes usually feature mild reaction conditions and good functional group tolerance. However, they usually require hazardous reagents like organotin or azo compounds.

A convenient microwave-promoted synthesis under mild and non-toxic conditions
Read more


http://www.chemistryviews.org/details/news/7297901/Trapping_Radicals_to_Make_Acylpyrroles.html

RAMELTEON

An efficient and practical process for the synthesis of ramelteon 1, a sedative-hypnotic, is described. Highlights in this synthesis are the usage of acetonitrile as nucleophilic reagent to add to 4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one 2 and the subsequent hydrogenation which successfully implement four processes (debromination, dehydration, olefin reduction, and cyano reduction) into one step to produce the ethylamine compound 13where dibenzoyl-l-tartaric acid is selected both as an acid to form the salt in the end of hydrogenation and as the resolution agent. Then, target compound 1 is easily obtained from13 via propionylation. The overall yield in this novel and concise process is almost twice as much as those in the known routes, calculated on compound 2.

A Novel and Practical Synthesis of Ramelteon

Sa Xiao , Chao Chen , Hongyan Li , Kuaile Lin , andWeicheng Zhou *

State Key Lab of New Drug & Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, State Institute of Pharmaceutical Industry, Shanghai 200437,China

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/op500386g

http://pubs.acs.org/doi/abs/10.1021/op500386g

Publication Date (Web): January 6, 2015

Copyright © 2015 American Chemical Society

*Telephone: +86 21 55514600. E-mail: zhouweicheng58@163.com.

NMR, IR MASS………http://pubs.acs.org/doi/suppl/10.1021/op500386g/suppl_file/op500386g_si_001.pdf

Preparation of (S)-N-[2-(1,6,7,8-Tetrahydro-2H-indeno[5,4-b] furan-8-yl)ethyl]propionamide(1).

GAVE

white solid of 1(1.570 g, 85% yield, 99.8% ee). Purity by HPLC 99.6%.

Mp: 115−116 °C(113−115°C in literature 1 ).

1 H−NMR(400 MHz, CDCl3):

δ 1.39 (t, 3H); 1.63 (m, 1H); 1.83 (m, 1H); 2.02 (m, 1H); 2.16 (dd, J=8, 2H); 2.28 (m, 1H); 2.78 (m, 1H); 2.83 (m, 1H); 3.14 (m, 1H); 3.22 (m, 2H); 3.33 (m, 2H); 4.54 (m, 2H); 5.38 (br s, 1H); 6.61 (d, J=8, 1H); 6.97 (d, J=8, 1H).

13C−NMR(100 MHz, CDCl3):

δ 173.85, 159.56, 143.26, 135.92, 123.52, 122.28, 107.56, 71.26, 42.37, 38.17, 33.66, 31.88, 30.82, 29.86, 28.73, 10.01.

MS (ES+): m/z 282(M+Na) + .

[α]D −57.3(c=1.0, CHCl3, −57.8 in literature 1 ).

Anal. (C16H21NO2) Calc: C, 74.10; H, 8.16; N, 5.40; found: 74.09; H, 8.17; N, 5.47.

References

(1) Uchikawa, O.; Fukatsu, K.; Tokunoh, R.; Kawada, M.; Matsumoto, K.; Imai, Y.; Hinuma, S.; Kato, K.; Nishikawa, H.; Hirai, K.; Miyamoto M.; Ohkawa, S. J. Med. Chem. 2002, 45, 4222-4239.

(2) Yamano, T.; Yamashita, M.; Adachi, M.; Tanaka, M.; Matsumoto, K.; Kawada, M.; Uchikawa, O.; Fukatsu, K.; Ohkawa, S. Tetrahedron: Asymmetry. 2006, 17, 184-190.

SHANGHAI

SHANGHAI CHINA

The Shanghai International Exhibition Center, an example of Soviet neoclassical architecture in Shanghai

Bulletin of the Chemical Society of Ethiopia

http://www.ajol.info/index.php/bcse


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Federal Democratic Republic of Ethiopia የኢትዮጵያ ፌዴራላዊ ዲሞክራሲያዊ ሪፐብሊክ ye-Ītyōṗṗyā Fēdēralāwī Dīmōkrāsīyāwī Rīpeblīk
Flag Emblem

Coins of the Axumite king Endybis, 227–235 AD, at the British Museum. The inscriptions in Ancient Greek read "AΧWMITW BACIΛEYC" ("King of Axum") and "ΕΝΔΥΒΙC ΒΑCΙΛΕΥC" ("King Endybis").

Mountain nyalas in Nechisar National Park, one of several wildlife reserves in Ethiopia.

EXAMPLE


Journal Home > Vol 29, No 1 (2015) > 

Regioselective iodination of aryl amines using 1,4-dibenzyl-1,4-diazoniabicyclo [2.2.2] octane dichloroiodate in solution and under solvent-free conditions

M. Alikarami, S. Nazarzadeh, M. Soleiman-Beigi

Abstract

1,4-Dibenzyl-1,4-diazoniabicyclo[2.2.2]octane dichloroiodate is an efficient and regioselective reagent for iodination of aryl amines. A wide variety of aryl amines in reaction with this reagent afforded regioselectively iodinated products. The iodination reaction can be carried out in solution or under solvent-free condition at room temperature.

KEY WORDS:  Regioselective iodination, Aryl amines, 1,4-Dibenzyl-1,4-diazoniabicyclo [2.2.2] octane dichloroiodate,  Solvent-free conditions

Bull. Chem. Soc. Ethiop. 2015, 29(1), 157-162

DOI: http://dx.doi.org/10.4314/bcse.v29i1.15

Full Text:

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"Pd/NHC-Catalyzed Enantiospecific and Regioselective Suzuki-Miyaura Arylation of 2-Arylaziridines: Synthesis of Enantioenriched 2-Arylphenethylamine Derivatives"

"Pd/NHC-Catalyzed Enantiospecific and Regioselective Suzuki-Miyaura Arylation of 2-Arylaziridines: Synthesis of Enantioenriched 2-Arylphenethylamine Derivatives"
Youhei Takeda*, Yuki Ikeda, Akinobu Kuroda, Shino Tanaka, and Satoshi Minakata*
J. Am. Chem. Soc. 2014, 136, 8544–8547. DOI: 10.1021/ja5039616 

* Highlighted in Org. Process Res. Dev. as "Some Items of Interest to Process R&D Chemists and Engineers"! !（link）
Abstract: A palladium-catalyzed stereospecific and regioselective cross-coupling of enantiopure 2-arylaziridines with arylboronic acids under mild conditions to construct a tertiary stereogenic center has been developed. N-heterocyclic carbene (NHC) ligands drastically promote the coupling, suppressing β-hydride elimination. The enantiospecific cross-coupling allowed us for preparation of a series of biologically important 2-arylphenethylamine derivatives in an enantiopure form.