A practical synthesis of 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid - The key precursor toward imatinib

Tetrahedron Letters

Volumn 53, Issue 38, 2012, Pages 5056-5058

  Koroleva, Elena V ^a   Kadutskii, Aleksey P ^b   Farina, Alexander V ^c   Ignatovich, Janna V ^a   Ermolinskaya, Anastasiya L ^a   Gusak, Klaudiya N ^a   Kalinichenko, Elena N ^c  

^a INSTITUTE OF CHEMISTRY OF NEW MATERIALS   (Belarus)

^b INSTITUTE OF PHYSICAL ORGANIC CHEMISTRY   (Belarus)

^c INSTITUTE OF BIOORGANIC CHEMISTRY   (Belarus)

Author keywords

4 (4 Methylpiperazin 1 yl)methyl benzoic acid; Benzyl derivatives; Imatinib; Reductive alkylation

Indexed keywords

1 METHYLPIPERAZINE; 4 [(4 METHYLPIPERAZIN 1 YL)METHYL]BENZOIC ACID; BENZOIC ACID DERIVATIVE; HETEROCYCLIC AMINE; IMATINIB; METHYL GROUP; PIPERAZINE DERIVATIVE; SODIUM DERIVATIVE; TRIACETOXYSODIUM BOROHYDRIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; LARGE SCALE PRODUCTION; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION; SCALE UP; SYNTHESIS;

EID: 84865193591     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.06.107     Document Type: Article

References (23)

1. Z. Szakacs, S. Beni, Z. Vagra, L. Orfi, G. Keri, and B. Noszal J. Med. Chem. 48 2005 249
2. E.V. Koroleva, K.N. Gusak, and Zh.V. Ignatovich Russ. Chem. Rev. 79 2010 655
3. Zimmermann, J. 0564409 B1, 1992;
4. Chem. Abstr. 1994, 120, 107056.
5. Loiseleur, O.; Kaufmann, D.; Abel, S.; Buerger, H.; Meisenbach M.; Schmitz, B.; Sedelmeier G. EP 1474408, 2003; Chem. Abstr. 2004, 139, 180080w.
6. P. Sairam, R. Puranic, A.S. Kelkar, S. Sasikiran, M. Veender, and A. Parvathi Synth. mmun. 33 2003 3597
7. A.S. Ivanov, and S.V. Shishkov Monatsh. Chem. 140 2009 619
8. H. Liu, W. Xia, and Yu. Luo Monatsh. Chem. 141 2010 907
9. J. Ignatovich, K. Gusak, T. Chernikhova, N. Kozlov, and E. Koroleva Chem. Heterocycl. Comp. 2007 1820
10. Zh.V. Ignatovich, K.N. Gusak, N.G. Kozlov, and E.V. Koroleva Russ. J. Org. Chem. 43 2007 1573
11. J. Ignatovich, K. Gusak, N. Kozlov, V. Kovalev, and E. Koroleva Arkivoc ix 2008 51
12. B.T. Cho, and S.K. Kang Tetrahedron 61 2005 5725
13. C.D. Gutierrez, V. Bavetsias, and E. McDonald Tetrahedron Lett. 46 2005 3595
14. V.A. Tarasevich, and N.G. Kozlov Russ. Chem. Rev. 68 1999 55
15. R.O. Hutchins, and D. Kandasamy J. Org. Chem. 46 1981 3571
16. A. Heydari, S. Khaksar, J. Akbari, M. Esfandyari, M. Pourayoubi, and M. Tajbakhsh Tetrahedron Lett. 48 2007 1135
17. A.F. Abdel-Magid, K.G. Carson, B.D. Harris, C.A. Maryanoff, and R.D. Shah J. Org. Chem. 61 1996 3849
18. B. Basu, S. Jha, M.H. Bhuiyan, and P. Das Synlett 2003 555
19. C.F. Lane Synthesis 1975 135
20. J. Brusses, R.A.T.M. van Benthe, C.G. Kruse, and A. Van der Gen Tetrahedron: Asymmetry 1 1990 163
21. S. Bhattacharyya J. Org. Chem. 60 1995 4928
22. S. Bhattacharyya, S. Chatterjee, and J.S. Williamson Synth. Commun. 1997 4265
23. I. Sahema, R. Borah, and J.C. Sarma J. Chem. Soc., Perkin Trans. 1 2000 503