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Synfacts 2017; 13(02): 0119
DOI: 10.1055/s-0036-1589893
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of BMS-741672

Rezensent(en):
Philip Kocienski
Deerberg J * et al. Bristol-Myers Squibb Company, New Brunswick, USA
Stereoselective Bulk Synthesis of CCR2 Antagonist BMS-741672: Assembly of an All-cis (S,R,R)-1,2,4-Triaminocyclohexane (TACH) Core via Sequential Heterogeneous Asymmetric Hydrogenations.

Org. Process Res. Dev. 2016;
20: 1949-1966
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Publikationsverlauf

Publikationsdatum:
18. Januar 2017 (online)

 
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Key words

BMS-741672 - CCR2 antagonist - diastereoselective hydrogenation - reductive amination - Curtius rearrangement - Freidinger lactamization

Significance

BMS-741672 is a chemotactic chemokine receptor 2 (CCR2) antagonist that is of interest for the treatment of inflammatory, cardiovascular, and metabolic diseases. A salient feature of the synthesis depicted is the construction of the all-cis 1,2,4-triaminocyclohexane core. This route delivered 50 kg of the target in 12 steps and in 9% overall yield.


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Comment

A platinum-catalyzed reduction of β-enaminoester A using (S)-α-methylbenzylamine as a low-cost chiral template and reductive amination of the 3,4-cis-disubstituted cyclohexanone F with a secondary amine on a sulfided platinum catalyst established the stereochemistry in the trisubstituted cyclohexane G.


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