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US 11,702,380 B2Granted
Synthesis of omecamtiv mecarbil
AssigneeAmgen Inc.
InventorsSebastien Caille, James Murray, Kyle Quasdorf, Hannah Nguyen, Maria Victoria Silva Elipe, Ari Elizabeth Ericson
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Abstract
Provided herein are synthetic methods for the preparation of intermediates that are utilized in the synthesis of omecamtiv mecarbil dihydrochloride.
Claims59
A process for synthesizing 2-fluoro-3-nitrotoluene (“FNT”) comprising
- (a1) admixing 2-fluorotoluene with one or more bases and a boronation reagent to form a boronic acid;
- and
- (b1) admixing the resulting boronic acid with iron nitrate or a hydrate thereof to form the FNT;
- or
- (a2) admixing 2-fluorotoluene with one or more bases and a boronation reagent to form a boronic acid;
- and
- (b2) admixing the resulting boronic acid with nitric acid to form the FNT.
4 more elements
A process for synthesizing 1-(bromomethyl)-2-fluoro-3-nitrobenzene comprising
- (a) admixing 2-fluoro-3-nitrotoluene (FNT) with a bromination agent in the presence of blue LED light to form a mixture of FNB and 1-(dibromomethyl)-2-fluoro-3-nitrobenzene
- (b) admixing the FNB/FNBr2 mixture with a dialkyl phosphite to form FNB;
- and
- (c) optionally purifying FNB formed in step (b) by (i) washing the FNB with a dialkylphosphite and a trialkylamine, or (ii) extracting the FNB with an organic solvent and washing with aqueous base.
1 more element
Dependencies are inferred from the claim text.