Solid-phase synthesis of 3-amino-2-pyrazolines

Tetrahedron Letters

Volumn 39, Issue 32, 1998, Pages 5845-5848

  Lyngsø, Lars O ^a   Nielsen, John ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRAZOLINE 3 AMINE DERIVATIVE; PYRAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL REACTION; DRUG CONJUGATION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0032490961     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01158-7     Document Type: Article

References (19)

1. 1 Plunkett, M.J., Ellman, J.A., Scientific American, 1997, 4, 54-59.
2. 2 For rewievs see: a) Hermkens, P.H.H., Otteaheijm, H.C.J., Rees, D.C., Tetrahedron, 1996, 52, 4527-4554. b) Hermkens, P.H.H., Ottenhetjm, H.C.J., Rees, D.C., Tetrahedron, 1997, 53, 5643-5678.
3. 2 For rewievs see: a) Hermkens, P.H.H., Otteaheijm, H.C.J., Rees, D.C., Tetrahedron, 1996, 52, 4527-4554. b) Hermkens, P.H.H., Ottenhetjm, H.C.J., Rees, D.C., Tetrahedron, 1997, 53, 5643-5678.
4. 3 a) Watson, S.P., Wilson, R.D., Judd, D.B., Richards, S.A., Tetrahedron Lett., 1997, 38, 9065-9068; b) Wilson, R.D., Watson, S.P., Richards, S.A., Tetrahedron Lett., 1998, 39, 2827-2830.
5. 3 a) Watson, S.P., Wilson, R.D., Judd, D.B., Richards, S.A., Tetrahedron Lett., 1997, 38, 9065-9068; b) Wilson, R.D., Watson, S.P., Richards, S.A., Tetrahedron Lett., 1998, 39, 2827-2830.
6. 4 Marzinzik, A.L., Felder, E.R., J. Org. Chem. 1998, 63, 723-727 and references on heterocycle chemistry cited therein.
7. 5 Nefzi, A., Ostresh, J.M., Houghten, R.A., Chem. Rev. 1997, 97, 449-472.
8. 6 a) Ivey, K.J., Am. J. Med., 1983, 75, 53-64; b) Nanra, R.S., ibid, 1983, 75, 70-81; c) Allison, M.C., Howatson, A.G., Torrance, C.J., Lee, F.D., Russell, R.I., N. Eng. J. Med., 1992, 327, 749-754.
9. 6 a) Ivey, K.J., Am. J. Med., 1983, 75, 53-64; b) Nanra, R.S., ibid, 1983, 75, 70-81; c) Allison, M.C., Howatson, A.G., Torrance, C.J., Lee, F.D., Russell, R.I., N. Eng. J. Med., 1992, 327, 749-754.
10. 6 a) Ivey, K.J., Am. J. Med., 1983, 75, 53-64; b) Nanra, R.S., ibid, 1983, 75, 70-81; c) Allison, M.C., Howatson, A.G., Torrance, C.J., Lee, F.D., Russell, R.I., N. Eng. J. Med., 1992, 327, 749-754.
11. 7 Tsuji, K., Nakamura, K., Konishi, N., Tojo, T., Ochi, T., Senoh, H., Matsuo, M., Chem. Pharm. Bull. 1997, 45, 987-995.
12. 8 Haviv, F., DeNet, R.W., Boulanger, W.A., Patent US 4370339, 1983, 6pp.
13. 3) δ 191 (formyl), 165 (amide).
14. 10 After cleaving of the compound from the Rink resin using 95%TFA/DCM, HPLC (LC-MS) were recorded on Micromass LC-Platform using Quatropole Analyser, APcI probe(atmospheric pressure, chonical ionization) and Masslynx software v.2.3 with YMC reverse-phase C-18 column, 100 × 4.6 I.D., S-3 um 120 A.
15. 11 Benjamin, D.M., McCormack, J.J., Gump, D.W., Anal. Chem. 1973, 45, 1531-1534.
16. 12 Maryanoff, B.E., Reitz, A.B., Chem Rev., 1989, 89, 863-927.
17. 13 The coupling was validated by HPLC-UV and HPLC-MS.
18. 14 After cleaving of the compound from the Rink resin using 95%TFA/DCM, HPLC-UV were recorded on Merck Hitachi Lachrom HPLC system, 3 μm Supelcosil ABZ plus column, UV detection at 240 nm.
19. 2O followed by 3 ml acetone), 3*3 ml acetone, 3*3 ml DCM and dried.