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.

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

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
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.

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

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

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

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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