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Judicious application of allyl protecting groups for the synthesis of 2-morpholin-4-yl-4-oxo-4H-chromen-8-yl triflate, a key precursor of DNA-dependent protein kinase inhibitors

Lookup NU author(s): Professor Bernard Golding, Professor Roger Griffin, Dr Ian Hardcastle

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Abstract

2- Morpholin4-yl-4-oxo-4H-chromen-8-yl2,2,2-trifluoromethanesulfonate is a key intermediate for the synthesis of the DNA-dependent protein kinase (DNA-PK) inhibitor 8-dibenzothiophen-4-yl-2-morpholin-4-yl-chromen-4-one(NU7441). Two improved methods for the synthesis of this triflate have been developed: (A) in 35% overall yield, through modification of the published route, and ( B) in 15% overall yield, by a new route employing a Baker - Venkataraman rearrangement to enable generation of the chromenone scaffold. Both syntheses depend on the judicious use of allyl protecting groups.


Publication metadata

Author(s): Aristegui SR, El-Murr MD, Golding BT, Griffin RJ, Hardcastle IR

Publication type: Article

Publication status: Published

Journal: Organic Letters

Year: 2006

Volume: 8

Issue: 26

Pages: 5927-5929

Date deposited: 12/05/2010

ISSN (print): 1523-7060

ISSN (electronic): 1523-7052

URL: http://dx.doi.org/10.1021/ol062297x

DOI: 10.1021/ol062297x

PubMed id: 17165896


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