|
HS Code |
717605 |
| Iupac Name | 6-Bromo-3-(1-methyl-1H-pyrazol-4-yl)-5-[(3R)-3-piperidinyl]pyrazolo[1,5-a]pyrimidin-7-amine |
| Molecular Formula | C16H21BrN8 |
| Molecular Weight | 405.30 g/mol |
| Appearance | Solid (exact color may vary; typically off-white to yellowish) |
| Solubility | Soluble in DMSO, limited solubility in water |
| Purity | Typically ≥98% (dependent on supplier) |
| Canonical Smiles | CN1C=CN=C1C2=NN3C=NC(C4CCCN4)=C(N3C2N)Br |
| Inchi | InChI=1S/C16H21BrN8/c1-22-10-12(8-20-22)14-23-21-13-9-25(16(18)24-14)15(17)19-11(13)7-6-2-4-5-3-6/h6,8-10,19H,2-5,7H2,1H3,(H2,18,24)/t6-/m1/s1 |
| Storage Conditions | Store at -20°C, protected from light and moisture |
| Synonyms | None widely established |
| Chemical Class | Pyrazolopyrimidine derivative |
As an accredited 6-Bromo-3-(1-Methyl-1H-Pyrazol-4-Yl)-5-(3R)-3-Piperidinylpyrazolo[1,5-A]Pyrimidine-7-Amine factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
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Every few years, research communities get thrown a curveball by chemistry breakthroughs that change what’s possible. Some molecules open up new doors in medicinal chemistry, sparking questions about what comes next. 6-Bromo-3-(1-Methyl-1H-Pyrazol-4-Yl)-5-(3R)-3-Piperidinylpyrazolo[1,5-A]Pyrimidine-7-Amine fits that mold. If you spend days wearing a lab coat—maybe running reactions late at night or troubleshooting tricky synthesis steps—this name might cause a sigh or a grin. At first glance, it looks like another heavy-duty compound, but beneath the surface, there’s a story about rigorous design and bold exploration.
Dig deep into current pharmaceutical research articles and you’ll keep seeing new challenges for targeting complex biological systems. Large, multi-ring heterocycles like this one don’t exist in nature by accident. Their design, especially with bromine at position 6 and a carefully chosen piperidinyl side chain at 5, embodies years of accumulated wisdom from medicinal chemists who learned that a single ring tweak can flip a molecule's profile from ordinary to exceptional.
Adding a methyl-pyrazole group doesn’t just bulk up the skeleton. It often creates room for fine-tuned interactions with enzyme binding pockets. The piperidinyl ring—with its flexible (3R) configuration—is more than a space-filler. Its stereochemistry matters; it separates so-so candidates from structures worth chasing. You see this style of molecular engineering often behind successful kinase inhibitors and high-affinity receptor ligands. This combination signals to any researcher that the compound could serve as a scaffold for small-molecule modulators, especially in fields where selectivity and in vivo performance mean everything.
No commentary about a research molecule escapes scrutiny if it glosses over practicality. Lab teams want reliable solubility profiles. Bromine at the 6-position, for example, could hint at a boost in lipophilicity, making the compound more membrane-permeable. Yet, strong heterocycles keep the core polar, often helping compounds cross biological barriers without causing unwanted off-target effects.
The compound’s model is rooted in pyrazolo[1,5-a]pyrimidine chemistry—a backbone that’s won favor in pharmaceutical circles for a good reason. It withstands a range of synthetic conditions without decomposing or scrambling, which makes iterative optimization less of a cruel guessing game. Analytical teams favor molecules like this because NMR and LC-MS traceability hold up across batches, supporting projects that demand meticulous record-keeping. From an operational perspective, ease of purification can be a major dealbreaker, but the presence of piperidinyl and methyl groups offers functional handles for targeted modification or clean-up if contaminants show up during work-up or scaling steps.
Anyone comparing this compound with old-guard, first-generation kinase inhibitors or classic CNS agents will spot immediate differences. The molecular heft—both in terms of weight and synthetic complexity—sets it above simple, flat aromatic scaffolds used in decades past. A combination of electron-rich pyrazoles and pyrimidines rarely passes through the same metabolic pathways as plain rings, promising more predictable metabolic stability or at the least a different set of degradation profiles for toxicologists to puzzle over.
Think about a typical project in drug discovery. Time and again, chemists face the problem of “flat” molecules showing weak selectivity. Here, introducing a fused, three-ring structure adorned with piperidinyl, bromine, and pyrazolyl gives researchers a springboard for SAR studies. Neat symmetry and clear positions for further substitution help chemists build potent analogs rapidly. Past experience has shown that such frameworks not only unlock new biological pathways but also let teams fine-tune properties like CNS penetration or reduce hERG liability, two perennial headaches in medicinal chemistry.
During late-stage development, I’ve seen teams benefit when their starting scaffolds avoided metabolic trouble hotspots—aromatic amines handily replaced by protected bicyclic cores, for example. This specific structure’s balance between rigidity and modifiable side chains means a project doesn’t stall after lead optimization. Whether aiming for a kinase, GPCR, or even a non-traditional protein target, having a modular scaffold like this one can shape a program’s future trajectory in ways generic structures can’t.
In medicinal chemistry, nothing moves forward without biological data, but getting to the point of a potent candidate means lots of organic grunt work. The architecture here tells a story of intent. Piperidinyl offers a known “handle” for tuning solubility and permeability. Bromine enables cross-coupling reactions, paving the way for rapid analog synthesis without risky conditions. Even just having the 1-methylpyrazole group can give teams a foothold in modifying non-polar characteristics or fitting snugly into hydrophobic binding sites—a trick often exploited for kinase or receptor modulation. The entire arrangement points to druglike intent, not just chemical curiosity.
Over the years, I’ve seen research groups sink months into scaffolds that proved too finicky or unstable, losing time and grant money. Features found in this compound—robust backbone, available exit vectors, and modular growth sites—save headaches. For all its apparent complexity, the molecule’s practical side means you can build SAR libraries efficiently, whether hunting for blockbusters or just aiming to prove a concept. Think about the value for structure-based design, too. Crystallographers prefer fused heterocycles with clear electron density that stand up to assorted mutation cycles, while computational teams benefit from predictable tautomers and conformers.
A lot of analogs in pharmaceutical research start with legacy scaffolds—indoles, pyridines, simple benzene rings. Those cores do a job, but adding layers of tough, branded heterocycles creates a platform that’s both adaptable and robust. Unlike most plug-and-play three-ring systems, having a piperidine ring with a specific (3R) orientation changes the game for receptor selectivity.
Older chemistries sometimes leaned on chance to dodge metabolic lets-down. Lesser substrates tempted fate by hoping their amines wouldn’t get oxidized or that their rings wouldn’t lactamize. Engineers of this scaffold learned from those mistakes. Robust bonds, less-prone to hydrolysis, and cleanly separated aromatic and aliphatic domains suggest a compound built to last through both in vitro and in vivo studies. In my own experience, deployment of such advanced heterocycles often marks the moment a program moves from me-too projects to first-in-class ambition.
Day-to-day drug discovery becomes a race against both time and ever-increasing regulatory scrutiny. A molecule can’t just “work”—it must be reproducible and survive hundreds of rounds of analytical testing. This compound’s mix of halogenation, rigid core, and strategically-placed side chains signals awareness of real-world challenges. Even solubility—one of the great causes of attrition for new compounds—looks more manageable given the balance of polar and lipophilic features. This blend matches lessons learned across multiple industry programs, where successful candidates rarely emerged from headline-grabbing structures but from disciplined, incremental improvements layered on trusted frameworks.
The difference here fits what I’ve experienced in teams optimizing for both drug-like properties and ease of analog synthesis. While overengineered molecules sometimes frustrate synthetic chemists with endless steps or poor yields, this one’s recognizable scaffolding means even junior chemists can plan logical routes, spot byproducts before they become unmanageable, and complete routes in reasonable timeframes. In practice, that translates to fewer surprises come scale-up.
Advancing from bench to clinic involves more than just clever design. Stability, toxicity, and metabolic quirks can all torpedo a project. Compounds with brominated aromatic rings can sometimes throw up red flags for metabolic studies, but informed placement avoids liability hotspots. The presence of a piperidinyl ring gives medicinal teams an anchor for tuning pharmacokinetics, and the pyrazolyl-pyrimidine backbone has a track record in the literature for resisting oxidative breakdown.
Often, roadblocks come from poor batch-to-batch consistency, difficult crystallization, or stubborn impurities. Here, standard chromatographic methods handle cleanup better, providing clarity for both process chemists and regulatory filings. I’ve seen countless teams forced to abandon a promising program due to impurities that just wouldn’t quit; designs like this, built on established core motifs, make it less likely you’ll run a project into the ground by sheer process frustration.
For toxicity, the risk-reward calculus is never far from mind. Not every new ring system offers a smooth path through preclinical testing. Drawing on broad industry data, systems featuring fused bicyclic cores with measured flexibility have produced fewer “surprises” in off-target screening, often because their predictable breakdown avoids the most reactive metabolites. The careful placement of functional groups—particularly the freely modifiable methyl-pyrazole and the non-aromatic piperidine—supports safer SAR exploration, letting experienced teams build out analogs without risking nasty byproducts.
Looking ahead, the major value of 6-Bromo-3-(1-Methyl-1H-Pyrazol-4-Yl)-5-(3R)-3-Piperidinylpyrazolo[1,5-A]Pyrimidine-7-Amine probably won’t come from just being a chemical novelty. The greatest advances tend to come from frameworks designed for iteration, not from re-inventing the wheel with every new campaign. With this structure, research teams gain a foothold for tailoring properties across a spectrum: from solubility and absorption to receptor affinity, selectivity, and metabolic bypass.
From my time analyzing SAR progress across multiple therapeutic areas, I’ve watched how well-designed heterocyclic cores—like this—build momentum for drug programs, especially by enabling both focused and broad series expansions. Teams working with such scaffolds often get to clinical candidates faster, not only because the chemistry stands up under scrutiny, but also because there’s less need to “fix” core issues as the project moves forward.
Innovation isn’t always about what’s flashiest or most exotic. The quiet power behind this molecule lies in knowing which levers to pull, where to tweak, and how to keep synthesis both accessible and reliable. By housing complexity within a manageable, modifiable architecture, the compound supports the kind of steady, iterative progress that underpins much of modern pharmaceutical discovery. As more public and private labs focus resources on efficiency and reproducibility, scaffolds built to last—and to be evolved—will keep finding their way into pipelines seeking competitive edges and faster routes to the clinic.
For those of us who grew up in crowded academic labs or spent years navigating the hurdles of medicinal chemistry, the arrival of compounds shaped by deep experience means more predictable success and fewer costly errors. 6-Bromo-3-(1-Methyl-1H-Pyrazol-4-Yl)-5-(3R)-3-Piperidinylpyrazolo[1,5-A]Pyrimidine-7-Amine may not become the next household name, but its thoughtful design signals a new era of rational drug design grounded in real-world industry needs.
As front-line researchers push toward targets that once seemed out of reach, compounds like this become more than just lines on a database; they represent hope for new treatments and evidence that chemistry is still built on both hard science and human ingenuity. Rather than chasing every shiny new scaffold, research teams now lean more on experience, selective innovation, and a willingness to learn from what works—and what doesn’t. In this light, molecules like 6-Bromo-3-(1-Methyl-1H-Pyrazol-4-Yl)-5-(3R)-3-Piperidinylpyrazolo[1,5-A]Pyrimidine-7-Amine point toward a productive future for both the bench chemist and the patients waiting at the other end of the pipeline.