This compound arises from reduction of the amide carbonyl in the upstream hydroxyacetamide precursor (Mirabegron EP Impurity G), converting the amide linkage to a secondary amine while retaining the nitro group. Subsequent catalytic transfer hydrogenation (ammonium formate, Pd/C) reduces the nitro group to an amine, yielding (R)-2-((4-aminophenethyl)amino)-1-phenylethan-1-ol --- the final intermediate before thiazole coupling completes mirabegron's structure. As a hydrochloride salt, this form offers improved crystallinity and handling stability for process chemistry and reference standard applications.
(R)-2-((4-Nitrophenethyl)amino)-1-phenylethan-1-ol hydrochloride, designated Mirabegron Impurity F, is a chiral secondary amine hydrochloride salt bearing a nitrophenyl substituent. It occupies a pivotal midpoint in the mirabegron synthetic pathway, positioned directly between the hydroxyamide precursor (EP Impurity G) and the diaminophenol intermediate that couples with the drug's thiazole fragment.
| Chemical Name | (R)-2-((4-Nitrophenethyl)amino)-1-phenylethanol Hydrochloride (Mirabegron Impurity F) |
| CAS Number | 521284-21-9 |
| IUPAC Name | (1R)-2-[[2-(4-Nitrophenyl)ethyl]amino]-1-phenylethan-1-ol Hydrochloride |
| Molecular Formula | C16H19ClN2O3 |
| Molecular Weight | 322.79 g/mol g/mol |
Central synthetic intermediate connecting the amide-reduction and nitro-reduction stages of mirabegron production.
Designated Mirabegron Impurity F for quality control testing and impurity profiling.
Used in ANDA/NDA filings requiring characterized process-related impurity reference materials.
Supports API manufacturing process development and analytical method validation.
J. Med. Chem.
Org. Process Res. Dev. (process chemistry reference)
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