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An improved synthesis of anticancer benzothiopyranoindazoles. An efficient large‐scale β‐aminoethylation procedure
Author(s) -
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
Publication year - 1991
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570280261
Subject(s) - chemistry , acylation , combinatorial chemistry , glycine , sequence (biology) , ring (chemistry) , scale (ratio) , stereochemistry , organic chemistry , amino acid , biochemistry , physics , quantum mechanics , catalysis
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.