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Development of a Practical Synthesis of a Functionalized Pyrrolo[2,1-f][1,2,4]triazine Nucleus

2012; American Chemical Society; Volume: 16; Issue: 11 Linguagem: Inglês

10.1021/op300252n

1520-586X

Bin Zheng, David A. Conlon, R. Michael Corbett, Melissa Chau, Dau-Ming Hsieh, Agnes Yeboah, Daniel S. Hsieh, Jale Müslehiddinoğlu, William P. Gallagher, Jeffrey N. Simon, Justin L. Burt,

Synthesis and Reactions of Organic Compounds

Functionalized pyrrolotriazine 1b is a key heterocyclic building block in the synthesis of BMS-690514, a potent anticancer agent. Described herein are our development activities that led to the efficient preparation of 1b on a large scale. The key transformations include a selective C-alkylation of an oxalacetate salt with a hydrazonyl bromide to form a 2-hydrazonoethyl-3-oxosuccinate, followed by cyclodehydration to an aminopyrrole. Subsequent deprotection and condensation with formamidine afforded the pyrrolotriazine scaffold. Further elaboration of this core provided the desired pyrrolotriazinyl amine.