New synthetic approach to 4-(3-aminopropyl)-5-amino-1-methylpyrazole starting from 3-cyanopyridine

Organic Process Research and Development

Volumn 10, Issue 1, 2006, Pages 159-162

  Ohigashi, Atsushi ^a   Temmaru, Kiyoshi ^b   Hashimoto, Norio ^a  

^a ASTELLAS PHARMA INC   (Japan)

^b KANEKA CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33344470489     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0501996     Document Type: Article

References (17)

1. Leanza, W. J.; Wildonger, K. J.; Miller, T. W.; Christensen, B. G. J. Med. Chem. 1979, 22, 1435.
2. Sunagawa, M.; Matsumura, H.; Takaasi, I.; Fukasawa, M.; Kato, M. J. Antibiot. 1990, 43, 519.
3. Smith, G. C. D. EP70706, January 26, 1983.
4. Wise, R.; Andrews, J. M.; Edwards, L. J. Antimicrob. Agents Chemother. 1983, 23, 559.
5. Ohki, H.; Okuda, S.; Yamanaka, T.; Ogino, T.; Kawabata, K.; Inoue, S.; Misumi, K.; Itoh, K.; Akamatsu, H.; Satoh, K. WO2002090364, November 14, 2002.
6. Hardegger, E.; Corrodi, H. Helv. Chim. Acta, 1956, 39, 984.
7. Dorn, H.; Zubek, A. Org. Synth. 1968, 48, 8.
8. Günter, E.; Phillipp, A. Angew. Chem., Int. Ed. Engl. 1974, 13, 206.
9. Nishihira, K.; Iwata, F.; Miyatake, T. JP01156963, September 28, 1988.
10. Rene, L.; Poncet, J.; Auzou, G. Synthesis 1986, 419.
11. Takamizawa, A.; Hayashi, S. Chem. Abstr. 1971, 74, 3617v.
12. Duaza, J. P.; Albright, J. D. US4393217, January 12, 1981.
13. Hirabayashi, S.; Ichihara, M.; Fujii, Y.; Furutera, T. JP07206826, November 30, 1994.
14. (a)Yamada, S.; Kikugawa, Y. Chem. Ind. 1966, 2169.
15. (b) Kikugawa, Y.; Kuramoto, M.; Saito, I.; Yamada, S. Chem. Pharm. Bull. 1973, 21, 1914.
16. 4 (2 g) in distilled water (970 mL) and acetonitrile (30 mL), flow rate: 1 mL/min., retention time: 2.2 min (9a) and 2.6 min (9b).
17. Ege, G.; Franz, H. J. Heterocycl. Chem. 1982, 19, 1267. The chemical shifts of 5-amino-1,4-dimethylpyrazole at the 3 position and 3-amino-1,4-dimethylpyrazole at the 5 position were 7.11 and 6.83 ppm, respectively.