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(Top) 1 Synthesis 2 See also 3 References 4 External links

Efaroxan

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Efaroxan

Clinical data

Routes of
administration

Oral

ATC code

none

Legal status

In general: uncontrolled

Identifiers

IUPAC name

2-(2-ethyl-2,3-dihydro-1-benzofuran-2-yl)-4,5-dihydro-1H-imidazole

CAS Number

89197-32-0^Y

PubChem CID

72016

ChemSpider

65015^Y

UNII

G00490L21H

ChEMBL

ChEMBL57895^Y

CompTox Dashboard (EPA)

DTXSID8045149

Chemical and physical data

Formula

C₁₃H₁₆N₂O

Molar mass

216.284 g·mol⁻¹

3D model (JSmol)

Interactive image

SMILES

N\1=C(\NCC/1)C3(Oc2ccccc2C3)CC

InChI

InChI=1S/C13H16N2O/c1-2-13(12-14-7-8-15-12)9-10-5-3-4-6-11(10)16-13/h3-6H,2,7-9H2,1H3,(H,14,15)^Y

Key:RATZLMXRALDSJW-UHFFFAOYSA-N^Y

(verify)

Efaroxan is an α₂-adrenergic receptor antagonist^[1] and antagonist of the imidazoline receptor.

Synthesis[edit]

Synthesis (Cmp#13):^[2] Revised:^[3]^[4]

The Darzens reaction between 2-fluorobenzaldehyde [57848-46-1] (1) and Ethyl 2-bromobutyrate [533-68-6] (2) gives ethyl 2-ethyl-3-(2-fluorophenyl)oxirane-2-carboxylate, CID:100942311 (3). A catalytic hydrogenation over Pd/C would give ethyl 2-[(2-fluorophenyl)methyl]-2-hydroxybutanoate, CID:77591056 (4). Saponification of the ester then gives 2-[(2-Fluorophenyl)methyl]-2-hydroxybutanoic acid, CID:53869347 (5). Treatment with 2 molar equivalents of sodium hydride apparently gives 2-Ethyl-2,3-dihydrobenzofuran-2-carboxylic acid [111080-50-3] (6). Treatment of the carboxylic acid with thionyl chloride then gives the acid chloride and subsequent treatment of this with ethylenediamine in the presence of trimethylaluminium completed the synthesis of Efaroxan (8).

References[edit]

^ Chopin P, Colpaert FC, Marien M (February 1999). "Effects of alpha-2 adrenoceptor agonists and antagonists on circling behavior in rats with unilateral 6-hydroxydopamine lesions of the nigrostriatal pathway". J. Pharmacol. Exp. Ther. 288 (2): 798–804. PMID 9918591.

^ Chapleo, Christopher B.; Myers, Peter L.; Butler, Richard C. M.; Davis, John A.; Doxey, John C.; Higgins, Stanley D.; Myers, Malcolm; Roach, Alan G.; Smith, Colin F. C. (1984). ".alpha.-Adrenoceptor reagents. 2. Effects of modification of the 1,4-benzodioxan ring system on .alpha.-adrenoreceptor activity". Journal of Medicinal Chemistry 27 (5): 570–576. doi:10.1021/jm00371a003.

^ Mayer, P.; Brunel, P.; Imbert, T. (1999). "A new efficient synthesis of efaroxan". Bioorganic & Medicinal Chemistry Letters 9 (20): 3021–3022. doi:10.1016/S0960-894X(99)00531-4.

^ Couture, K.; Gouverneur, V.; Mioskowski, C. (1999). "A new approach to the synthesis of efaroxan". Bioorganic & Medicinal Chemistry Letters 9 (20): 3023–3026. doi:10.1016/S0960-894X(99)00530-2.