An improved synthesis of anticancer benzothiopyranoindazoles. An efficient large-scale β-aminoethylation procedure

• Published in: Journal of heterocyclic chemistry Vol. 28; no. 2; pp. 517 - 527
• Main Authors: Beylin, Vladimir G., Colbry, Norman L., Giordani, Anne B., Goel, Om P., Johnson, Donald R., Leeds, Robert L., Leja, Boguslawa, Lewis, Edward P., Lustgarten, David M., Showalter, H. D. Hollis, Sercel, Anthony D., Reily, Michael D., Uhlendorf, Susan E., Zisek, Katherine A., Mcdonnell, Peter
• Format: Journal Article
• Language: English
• Published: Hoboken Wiley-Blackwell 01-02-1991; Wiley‐Blackwell; HeteroCorporation
• Subjects: Chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Organic chemistry; Preparations and properties; Phenols; Sulfur nitrogen heterocycle; Aromatic compound; Amine; Tetracyclic compound
• ISSN: 0022-152X; 1943-5193
• DOI: 10.1002/jhet.5570280261

Improved processes for the synthesis of bulk quantities of the benzothiopyranoindazole clinical agent CI‐958 and A‐ring congeners is reported. The process chosen for scale‐up operations achieves β‐aminoethylation of an anilino precursor via a three‐step sequence (acylation, reduction, deprotection) starting from N‐(trityl)glycine. Detailed analytical data are reported for the target compounds and most intermediates, and detailed spectroscopy is given for CI‐958.