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ORGANIC SPECTROSCOPY

Read all about Organic Spectroscopy on ORGANIC SPECTROSCOPY INTERNATIONAL 

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with AFRICURE PHARMA, ROW2TECH, NIPER-G, Department of Pharmaceuticals, Ministry of Chemicals and Fertilizers, Govt. of India as ADVISOR, earlier assignment was with GLENMARK LIFE SCIENCES LTD, as CONSUlTANT, Retired from GLENMARK in Jan2022 Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 32 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 32 PLUS year tenure till date Feb 2023, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 100 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 100 Lakh plus views on dozen plus blogs, 227 countries, 7 continents, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 38 lakh plus views on New Drug Approvals Blog in 227 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc He has total of 32 International and Indian awards

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A Method to Identify Best Available Technologies (BAT) for Hydrogenation Reactors in the Pharmaceutical Industry

January 2, 2015 2:30 pm / Leave a comment


J. Flow Chem. 2012, 2(3), 77–82

http://www.akademiai.com/content/8652651g3378x686/?p=ab7c1bc4cd7740e1855623297649f542&pi=3

http://www.akademiai.com/content/8652651g3378x686/fulltext.pdf

Journal of Flow Chemistry
Publisher Akadémiai Kiadó
ISSN 2062-249X (Print)
2063-0212 (Online)
Subject Flow Chemistry
Issue Volume 2, Number 3/September 2012
Pages 77-82
DOI 10.1556/JFC-D-12-00014
Authors
Tuong Doan1, Petr Stavárek1, Claude Bellefon1 Email for claude.debellefon@lgpc.cpe.fr* Author for correspondence: claude.debellefon@lgpc.cpe.fr

1CNRS, CPE Lyon University of Lyon Villeurbanne France

Abstract

A methodology that may be applied to help in the choice of a continuous reactor is proposed. In this methodology, the chemistry is first described through the use of eight simple criteria (rate, thermicity, deactivation, solubility, conversion, selectivity, viscosity, and catalyst). Then, each reactor type is also analyzed from their capability to answer each of these criteria. A final score is presented using “spider diagrams.” Lower surfaces indicate the best reactor choice. The methodology is exemplified with a model substrate nitrobenzene and a target pharmaceutical intermediate, N-methyl-4-nitrobenzenemethanesulphonamide, and for three different continuous reactors, i.e., stirred tank, fixed bed, and an advanced microstructured reactor. Comparison with the traditional batch reactor is also provided.

Fanetizole

January 1, 2015 2:15 pm / Leave a comment


Fanetizole structure.png

Fanetizole

Fanetizole shows immunoregulating activity.
RN: 79069-95-7

 

Fanetizole mesylate [USAN]

CP-48,810-27
Fanetizole mesylate
UNII-D3OG7B0G4M

Synthesis

Thioureas serve as a convenient starting material for 2-aminothiazoles.

Fanetizole synthesis.

Reaction of β-phenethylamine with ammonium isothiocyanate gives the corresponding thiourea. Treatment of that product with phenacyl bromide thus affords the thiazole product.[1]

  1. Lombardino, J. G.; 1981, U.S. Patent 4,307,106

Fanetizole.png

Systematic (IUPAC) name
4-Phenyl-N-(2-phenylethyl)-1,3-thiazol-2-amine
Clinical data
Legal status
?
Pharmacokinetic data
Protein binding %
Identifiers
CAS number 79069-94-6
ATC code ?
PubChem CID 54339
ChemSpider 49083
UNII BH48F620JA Yes
Chemical data
Formula C17H16N2S 
Mol. mass 280.39 g/mol

………………………………………….

Journal of the Chinese Chemical Society, 2009, 56, 455-458

http://proj3.sinica.edu.tw/~chem/servxx6/files/paper_10990_1246593848.pdf

Fanetizole (3j)
mp 114-115 C (Lit.,30 116-117 C). IR (KBr) :3192, 2957, 1562, 1481, 1445, 1332, 698 cm-1;

1H NMR(CDCl3) : 2.81 (t, J = 7.4 Hz, 2H), 3.42 (dd, J = 6.8, 10.8
Hz, 2H), 6.32 (s, 1H), 6.64 (s, 1H), 7.08 (d, J = 6.8 Hz, 2H),
7.15-7.28 (m, 4H), 7.34-7.37 (m, 2H), 7.77-7.80 (m, 2H).

30=. Potewar, T. M.; Ingale, S. A.; Srinivasan, K. V. Tetrahedron
2008, 64, 5019-5022.

…………………………………………

A remarkably high-speed solution-phase combinatorial synthesis of 2-substituted-amino-4-aryl thiazoles in polar solvents in the absence of a catalyst under ambient conditions and study of their antimicrobial activities
ISRN Organic Chemistry (2011), 434613, 6 pp. Publisher: (Hindawi Publishing Corp., )

http://www.hindawi.com/journals/isrn/2011/434613/

 

 

 

 

 

 

……………………………………………

Fanetizole
Ley et al  had previously developed a tube-in-tube reactor based on a semipermeable polymer membrane to  enable the transfer of gases into liquid flow streams. and here, we demonstrate the scalability and throughput of this reactor when used with ammonia gas. This was made possible by a the inclusion of a titration method to assess parameters including the liquid and gas configuration, reactor temperatures, flow rates, and solvent polarity. These data were then employed in a scaling-up process affording alkyl thioureas which were ultimately used in a telescoped procedure for the preparation of anti-inflammatory agent fanetizole on a multigram scale.

op-2013-00152r_0013

Researchers at Cambridge have shown how it is possible to calibrate a ‘tube-in-tube’ reactor containing ammonia gas using a simple in-line colourimetric titration technique.

This information was then used to deliver an ammonia solution of stoichiometrically to effect the telescoped 2 stage synthesis of the anti-inflammatory agent Fanetizole.

The automated continuous flow synthesiser was able to produce drug substance at a rate of approximately 10 g per hour, isolating the product by direct precipitation from the outflow reaction stream.

Fanetizole: Scaling-up of continuous flow processes with gases using a tube-in-tube reactor: in-line titrations and fanetizole synthesis with ammonia J. Pastre, D.L. Browne, M. O’Brien and S.V. Ley, Org. Proc. Res. Dev. 2013, 17, 1183-1191.

http://pubs.acs.org/doi/full/10.1021/op400152r

N-Phenethyl-4-phenylthiazol-2-amine: fanetizole (4):
mp: 116.3–117.5 °C (lit. 116–117 °C);(22)Potewar, T. M.; Ingale, S. A.; Srinivasan, K. C. Tetrahedron 2007, 63, 11066

[CrossRef], [CAS]
IR (cm–1, thin film): 1602, 1585, 1424, 1332, 773, 743, 697;
1H NMR (400 MHz, CDCl3): δ 7.85 (d, J = 7.3 Hz, 2H), 7.49–7.13 (m, 8H), 6.72 (s, 1H), 6.00 (br s, 1H), 3.55 (m, 2H), 2.94 (t, J = 7.1 Hz, 2H);
13C NMR (100 MHz, CDCl3): δ 169.5 (C0), 151.5 (C0), 138.5 (C0), 134.9, 128.7 (CH), 128.6 (CH), 128.5 (CH), 127.6 (CH), 126.5 (CH), 126.0 (CH), 100.6 (CH), 47.2 (CH2), 35.4 (CH2);
HRMS (ESI+) m/z: Calcd for C17H17N2S [M + H+] 281.1107, found 281.1100.

………………………..

A Hantzsch synthesis of 2-aminothiazoles performed in a heated microreactor system

*Corresponding authors
aGlaxoSmithKline Pharmaceuticals, New Frontiers Science Park (North), Essex, Harlow, UK
E-mail: Eduardo_2_Garcia-Egido@gsk.com;
Fax: +44 (0)1279 622500 ;
Tel: +44 (0)1279 627993
Lab Chip, 2002,2, 31-33

DOI: 10.1039/B109360F…….http://pubs.rsc.org/en/content/articlelanding/2002/lc/b109360f/unauth#!divAbstract

..This paper presents the first example known to the authors of a heated organic reaction performed on a glass microreactor under electro-osmotic flow control. The experiments consisted of the preparation of a series of 2-aminothiazoles by means of a Hantzsch reaction of ring-substituted 2-bromoacetophenones and 1-substituted-2-thioureas carried out in microchannels, with the aim of investigating the generic utility of the reactor in carrying out analogue reactions. The reactions were performed on T-design microchips etched into a thin borosilicate glass plate and sealed over with a thick borosilicate top plate containing reservoirs. The mobility of the reagents and products was achieved using electro-osmotic flow (EOF), with the driving voltages being generated by a computer-controlled power supply. During the experiments the T-shaped chip was heated at 70 °C using a Peltier heater, aligned with the channels and the heat generated by this device was applied to the lower plate. The degree of conversion was quantified by LC-MS using UV detection by comparison with standard calibration curves for starting materials and final products. In all cases, conversions were found to be similar or greater than those found for equivalent macro scale batch syntheses, thus illustrating the potential of this heated microreactor system to generate a series of compounds which contain biologically active molecules.

………………………………

Bioorganic and Medicinal Chemistry Letters, 1996 ,  vol. 6,   12  pg. 1409 – 1414

http://www.sciencedirect.com/science/article/pii/0960894X96002417

Full-size image (1 K)

 

………………………………………

ref

Heterocycles, 2010 ,  vol. 81,   12  pg. 2849 – 2854

Journal of the Chinese Chemical Society, 2009 ,  vol. 56,  3  pg. 455 – 458

Bioorganic and Medicinal Chemistry Letters, 1996 ,  vol. 6,   12  pg. 1409 – 1414

Pfizer Patent: DD144055DE2922523 , 1979 ;Chem.Abstr.,  vol. 92,  111001

Organic Process Research and Development, 2013 ,  vol. 17,   9  pg. 1183 – 1191

Tetrahedron, 2007 ,  vol. 63,   45  pg. 11066 – 11069

Tetrahedron, 2008 ,  vol. 64,  22  pg. 5019 – 5022

NEW DRUG APPROVALS…….One lakh viewers in USA

January 1, 2015 4:25 am / 4 Comments on NEW DRUG APPROVALS…….One lakh viewers in USA


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