Every now and then, a relatively simple molecule turns out to punch well above its weight in drug discovery. CAS 7499-19-6 — 2-methyl-3-phenylpropanamide — is exactly that kind of compound. Despite its modest structure (C₁₀H₁₃NO, MW 163.22), this primary amide shows up across a surprising range of therapeutic areas, from antivirals to CNS disorders and pulmonary disease.
What Is It?
2-Methyl-3-phenylpropanamide (also called 2-methyl-2-phenylpropionamide) is a benzylic amide — essentially a propionamide backbone with a methyl branch and a phenyl ring attached. It has a melting point of 106 °C, a predicted LogP of 1.6 (moderately lipophilic), and one hydrogen bond donor/acceptor pair — a profile that sits comfortably in drug-like chemical space (Lipinski territory).
Where Does It Show Up in the Literature?
Wikipedia doesn’t have a dedicated page for this CAS number — the molecule is too niche for a standalone entry. But a deeper dive into the patent and journal literature tells a different story:
- Antiviral research (HIV): Two separate WO patents from PharmaResources Shanghai (WO2012065062A1, WO2013006792A1) feature this scaffold as part of novel antiviral compound families, targeting HIV replication pathways. The amide motif appears central to the pharmacophore.
- CNS disorders: Janssen Pharmaceuticals patented a series of GlyT2 inhibitors (WO2005044810A1) built around α-, β-, and ɣ-amino acid derivatives — and 2-methyl-3-phenylpropanamide fits squarely in that structural class. Target indications include muscle spasticity, tinnitus, epilepsy, and neuropathic pain.
- Rho kinase inhibition: Chiesi Farmaceutici’s patent US20180215758A1 describes tyrosine amide derivatives as ROCK inhibitors for pulmonary diseases (asthma, COPD, IPF, PAH). The amide backbone in CAS 7499-19-6 is a recurring motif in their scaffold.
- Substituted imidazole carboxamides: WO2021055612A1 covers a broad family of imidazole carboxamides for cancer, lysosomal storage disorders, and neurodegenerative conditions — again featuring this amide as a building block.
A Building Block, Not Just a Reagent
What makes this compound interesting isn’t exotic reactivity — it’s the scaffold utility. The amide group offers a handle for further derivatization (hydrolysis to the acid, reduction to the amine, or direct coupling in peptide-like constructs), while the phenyl ring opens up π-stacking and hydrophobic interactions in target binding pockets. It’s the kind of intermediate that medicinal chemists keep in their “reliable go-tos” drawer.
From a synthesis standpoint, the compound can be prepared via palladium-catalyzed hydroaminocarbonylation of alkenes using NH₄Cl as a cheap ammonia surrogate (Bao Gao et al., Chem. Sci., 2018), or through classical amide coupling from 2-benzylpropionic acid.
Bottom Line
CAS 7499-19-6 may not have a Wikipedia page (yet), but it’s earned its place in the synthetic chemist’s toolbox. If you’re working on CNS targets, antiviral projects, or kinase inhibitor programs, this is one to keep on your radar.
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