Identification and Development of an Efficient Route to SB-649915

…, M Kingswood, M Loft, S Moore, S Smith…

Index: Armitage, Mark; Bret, Guillaume; Choudary, Bernie M.; Kingswood, Mike; Loft, Mike; Moore, Steve; Smith, Steve; Urquhart, Michael W. J. Organic Process Research and Development, 2012 , vol. 16, # 10 p. 1626 - 1634

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Citation Number: 6

Abstract

The discovery and development of an efficient manufacturing route to the SSRI-5-HT1A receptor antagonist 6-[(1-{2-[(2-methyl-5-quinolinyl) oxy] ethyl}-4-piperidinyl) methyl]-2 H-1, 4-benzoxazin-3 (4 H)-one (SB-649915) 1 is described. The existing route to 1 involved coupling quinoline 6 with piperidine 5 and was considered lengthy as a consequence of the nine synthetic steps required to prepare 5. Two new routes to the key piperidine ...