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Process Development of 5-Fluoro-3-[3-[4-(5-methoxy-4-pyrimidinyl)-1- piperazinyl]propyl]-1 H -indole Dihydrochloride

1997; American Chemical Society; Volume: 1; Issue: 4 Linguagem: Inglês

10.1021/op970213h

1520-586X

Neal G. Anderson, Thomas D. Ary, James L. Berg, Peter J. Bernot, Yeung Chan, Chien‐Kuang Chen, Merrill L. Davies, John D. DiMarco, Ronald D. Dennis, R.P. Deshpande, Dinh-Dai Hoang, Roberto Droghini, William Early, Jack Z. Gougoutas, John A. Grosso, John Harris, Oscar W. Haas, Paul A. Jass, Daniel H. Kim, Gus A. Kodersha, Atul S. Kotnis, Jean Lajeunesse, David A. Lust, Gary D. Madding, Sandeep Modi, Jerome L. Moniot, Andrew L. Nguyen, Venkatapuram A. Palaniswamy, Douglas W. Phillipson, James H. Simpson, D. Thoraval, David A. Thurston, Kai Tse, Robert E. Polomski, Donald L. Wedding, William J. Winter,

Synthesis and Reactions of Organic Compounds

5-Fluoro-3-[3-[4-(5-methoxy-4-pyrimidinyl)-1-piperazinyl]propyl]-1H-indole dihydrochloride (1) facilitates 5-HT neurotransmission and was an antidepressant drug candidate. The development of a safe, rugged process for the large-scale, chromatography-free preparation of this compound is described. The main areas of optimization included a Fischer indole synthesis, preparation and chlorination of a monohydroxypyrimidine, and coupling of the resultant fragments to prepare the drug substance.