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1-{[Benzyl-(2-cyano-ethyl)-amino]-methyl}-5-methyl-1H-pyrazole-3-carboxylic acid methyl ester
 
 
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Short Note

1-{[Benzyl-(2-cyano-ethyl)-amino]-methyl}-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester

by
Leila Herrag
1,2,*,
Rachid Touzani
1,3,
Abdelkrim Ramdani
1 and
Belkheir Hammouti
1
1
Laboratoire de Chimie Organique Physique, Département de Chimie , Faculté des Sciences , Université Mohammed Premier , B.P. 524, 60000 Oujda , Maroc
2
Laboratoire de Chimie des Eaux et Corrosion, Département de Chimie, Faculté des Sciences, B.P. 717, Oujda, Maroc
3
Université Mohammed Premier, Faculté Pluridisciplinaire de Nador B.P. 300, 62700 Selouane, Nador, Maroc
*
Author to whom correspondence should be addressed.
Molbank 2006, 2006(5), M494; https://doi.org/10.3390/M494
Submission received: 19 July 2006 / Accepted: 31 July 2006 / Published: 1 September 2006
The products of aza-type Michael addition, i.e., β-amino carbonyl compounds and their derivatives, are often used as peptide analogs or precursors of optically active amino acids, amino alcohols, diamines, and lactams [1]. Moreover, β-amino carbonyl functionalities are ubiquitous motifs in natural products such as alkaloids and polyketides [2]. Herein, we report the synthesis of new product using aza-type Michael reactions under mild conditions.
Molbank 2006 m494 i001
A mixture of 3-(benzylamino)propionitrile 1 [3] (1g, 6.25mmol) and 1-hydroxymethyl-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester 2 [4] (1.15g , 6.25 mmol) in 20 ml of acetonitrile was stirred at room temperature for four days, then the mixture was dried with Na2SO4 and filtered. The solvent was evaporated under reduced pressure. The product 3 obtained with an 81% yield as yellow oil.
1H-NMR (300 MHz, CDCl3): δ= 7.34 (CHarom, 5H, s) ; 6.55 ( CHpyr, 1H, s) ; 4.94 (pyr-CH2-N, 2H, s) ; 4.33-4.4 ( OCH2 , 2H, q, J = 8Hz) ; 3.750 (C6H5-CH2, 2H, s) ; 3.00-3.1 (CH2-CH2-CN, 2H, t, J = 7.33Hz) ; 2.34-2.38 ( N-CH2, 2H, t, J = 8Hz); 2.18 (CH3, 3H, s) and 1.39-1.34 ( CH3, 3H, t, J = 8Hz).
13C-NMR (CDCl3, 75 MHz): δ= 162.94 (l); 143.26 (i); 141.432 (g); 137.51 (m); 129.16; 129.06 (n); 128.83 (f); 128.23 (o); 119.00 (a); 109.19 (h); 67.70 (e); 61.26 (k); 56.76 (d); 48.34 (c); 17.44 (b); 14.77 (p); 11.55 (j).
EI-MS (70 eV, m/z): 173; 171; 154 (51.4); 119; 91 (60.6).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

  1. Fustero, S.; Pina, B.; Salavert, E.; Navarro, A.; Ramirez de Arellano, M. C.; Fuentes, A. S. J. Org. Chem. 2002, 67, 4667. [PubMed]
  2. Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed 1998, 37, 1045.
  3. Xu, L.W.; Li, L.; Xia, C.-G. Helvetica Chimica Acta 2004, 87, 1522.Azizi, N.; Saidi, M. R. Tetrahedron 2004, 60, 383.
  4. Touzani, R.; Ramdani, A.; El Kadiri, S.; Gourand, F. Molecules 1999, 4, M116.

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MDPI and ACS Style

Herrag, L.; Touzani, R.; Ramdani, A.; Hammouti, B. 1-{[Benzyl-(2-cyano-ethyl)-amino]-methyl}-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester. Molbank 2006, 2006, M494. https://doi.org/10.3390/M494

AMA Style

Herrag L, Touzani R, Ramdani A, Hammouti B. 1-{[Benzyl-(2-cyano-ethyl)-amino]-methyl}-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester. Molbank. 2006; 2006(5):M494. https://doi.org/10.3390/M494

Chicago/Turabian Style

Herrag, Leila, Rachid Touzani, Abdelkrim Ramdani, and Belkheir Hammouti. 2006. "1-{[Benzyl-(2-cyano-ethyl)-amino]-methyl}-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester" Molbank 2006, no. 5: M494. https://doi.org/10.3390/M494

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