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Fanetizole

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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

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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.

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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/

 

 

 

 

 

 

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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. Dev201317, 1183-1191.

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

N-Phenethyl-4-phenylthiazol-2-amine: fanetizole (4):
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.

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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.

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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)

 

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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


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