The preparation of 2,4-disubstituted thiazoles on solid support

Tetrahedron Letters

Volumn 40, Issue 3, 1999, Pages 423-426

  Goff, Dane ^a,b   Fernandez, Juan ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

^b RIGEL PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NITRILE; THIAZOLE DERIVATIVE; THIOAMIDE;

ARTICLE; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033555661     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02392-2     Document Type: Article

References (7)

1. Kearney, P.C.; Fernandez, M.; Flygare, J.A. J. Org. Chem. 1998, 63, 196-200.
2. Shabana, R.; Meyer, H.J.; Lawesson, S.O. Phosphorous and Sulfur 1985, 25, 297-305.
3. HPLC was performed on a Waters Millenium system using an Alltech Alltima C-18 reversed phase column 4.6 x 250 mm. The flow rate was 1.0 ml/min, injection volume 2-10μl. The linear gradient used was 5% acetonitrile to 81% acetonitrile in water over 36 min, then increasing to 100% acetonitrile over 4 min. Both solvents contained 0.1% TFA by volume. UV detection was at 220 and 254 nm.
4. Zuckermann, R.N.; Kerr, J.M; Kent, S.B.; Moos, W.H. J. Amer. Chem. Soc. 1992, 114, 10646-10647.
5. Marzoni, G. J. Heterocyclic Chem. 1986, 23, 577-580.
6. 2O for 20 min. The resin was filtered off and washed with dichloromethane. The filtrate was concentrated in vacuo and lyophilized from acetonitrile/water to give 8a.
7. Commercially available bifunctional nitriles include 3- and 4-cyanobenzenesulfonyl chloride, 3- and 4-cyanophenyl isocyanate, 3- and 4-cyanophenol as well as the 3- and 4-cyanobenzoic acids and the corresponding acid chlorides. Other useful building blocks such as the 3- or 4-cyanobenzylamines can be prepared from the commercially availablebenzyl halides.