Organic Process Research and Development, volume 16, issue 10, pages 1626-1634
Identification and Development of an Efficient Route to SB-649915
Mark Armitage
1
,
Guillaume Bret
1
,
Bernie M Choudary
1
,
Mike Kingswood
1
,
Mike Loft
1
,
Steve Moore
1
,
Steve Smith
1
,
Michael W J Urquhart
1
1
Glaxo Group Limited, Medicines Research Centre, Gunnels
Wood Road, Stevenage, Hertfordshire, SG1 2NY, U.K.
|
Publication type: Journal Article
Publication date: 2012-10-02
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.4
ISSN: 10836160, 1520586X
Organic Chemistry
Physical and Theoretical Chemistry
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]-2H-1,4-benzoxazin-3(4H)-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 intermediate 5 are identified which deliver this compound in five and two steps respectively, from readily available materials using novel lithiation and Friedel–Crafts methodology respectively. The latter of these two routes was successfully demonstrated at 5 L scale to deliver 700 g of 5. Development to the methanesulfonate 34, an alternative to quinoline 6, is also described as is the final alkylation of piperidine 5 with this methanesulfonate 34 to deliver SB-649915 1.
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Citations by publishers
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Armitage M. et al. Identification and Development of an Efficient Route to SB-649915 // Organic Process Research and Development. 2012. Vol. 16. No. 10. pp. 1626-1634.
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Armitage M., Bret G., Choudary B. M., Kingswood M., Loft M., Moore S., Smith S., Urquhart M. W. J. Identification and Development of an Efficient Route to SB-649915 // Organic Process Research and Development. 2012. Vol. 16. No. 10. pp. 1626-1634.
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TY - JOUR
DO - 10.1021/op300185s
UR - https://doi.org/10.1021/op300185s
TI - Identification and Development of an Efficient Route to SB-649915
T2 - Organic Process Research and Development
AU - Armitage, Mark
AU - Bret, Guillaume
AU - Choudary, Bernie M
AU - Kingswood, Mike
AU - Loft, Mike
AU - Moore, Steve
AU - Smith, Steve
AU - Urquhart, Michael W J
PY - 2012
DA - 2012/10/02 00:00:00
PB - American Chemical Society (ACS)
SP - 1626-1634
IS - 10
VL - 16
SN - 1083-6160
SN - 1520-586X
ER -
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@article{2012_Armitage,
author = {Mark Armitage and Guillaume Bret and Bernie M Choudary and Mike Kingswood and Mike Loft and Steve Moore and Steve Smith and Michael W J Urquhart},
title = {Identification and Development of an Efficient Route to SB-649915},
journal = {Organic Process Research and Development},
year = {2012},
volume = {16},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/op300185s},
number = {10},
pages = {1626--1634},
doi = {10.1021/op300185s}
}
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Armitage, Mark, et al. “Identification and Development of an Efficient Route to SB-649915.” Organic Process Research and Development, vol. 16, no. 10, Oct. 2012, pp. 1626-1634. https://doi.org/10.1021/op300185s.