Production Method 1

75-98-9

86847-64-5

Reaction Conditions

1.1 Reagents: Oxalyl chloride Catalysts: Dimethylformamide Solvents: Dichloromethane ;  0 °C
2.1 Reagents: Triethylamine Solvents: Tetrahydrofuran ;  0 °C; 1 h, 0 °C → rt
3.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  -20 °C → 0 °C; 2 h, 0 °C
3.2 0 °C; 2 h, 0 °C → rt

Reference

Regioselective ketone α-alkylation with simple olefins via dual activation

Mo, Fanyang; et al, Science (Washington, 2014, 345(6192), 68-72

Production Method 2

86847-59-8

86847-64-5

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  -20 °C → 0 °C; 2 h, 0 °C
1.2 0 °C; 2 h, 0 °C → rt

Reference

Regioselective ketone α-alkylation with simple olefins via dual activation

Mo, Fanyang; et al, Science (Washington, 2014, 345(6192), 68-72

Production Method 3

86847-64-5

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Tetrahydrofuran ;  0 °C; 1 h, 0 °C → rt
2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  -20 °C → 0 °C; 2 h, 0 °C
2.2 0 °C; 2 h, 0 °C → rt

Reference

Regioselective ketone α-alkylation with simple olefins via dual activation

Mo, Fanyang; et al, Science (Washington, 2014, 345(6192), 68-72

N-(3-formyl-2-pyridinyl)-2,2-dimethylpropanamide Raw materials

• 2,2-dimethylpropanoic acid
• 2-Pivalamidopyridine

N-(3-formyl-2-pyridinyl)-2,2-dimethylpropanamide Preparation Products

• N-(3-formyl-2-pyridinyl)-2,2-dimethylpropanamide (86847-64-5)

• 1. Enabling high-throughput single-animal gene-expression studies with molecular and micro-scale technologies
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• 4. Evidence of pre-micellar aggregates in aqueous solution of amphiphilic PDMS–PEO block copolymer?
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• 5. Estimates of hydride ion stability in condensed systems: energy of formation and solvation in aqueous and polar-organic solvents
  Craig A. Kelly,David R. Rosseinsky Phys. Chem. Chem. Phys., 2001,3, 2086-2090

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Pyridine carboxaldehydes

Recent Advances in the Study of N-(3-formyl-2-pyridinyl)-2,2-dimethylpropanamide (CAS: 86847-64-5)

N-(3-formyl-2-pyridinyl)-2,2-dimethylpropanamide (CAS: 86847-64-5) has recently emerged as a compound of significant interest in chemical biology and pharmaceutical research. This heterocyclic amide derivative, featuring both pyridine and pivalamide moieties, has demonstrated promising potential in medicinal chemistry applications. Recent studies have focused on its role as a key intermediate in the synthesis of biologically active molecules, particularly in the development of kinase inhibitors and anti-inflammatory agents.

Structural analyses reveal that the 3-formyl group on the pyridine ring provides an essential reactive site for further chemical modifications, while the 2,2-dimethylpropanamide moiety contributes to the compound's stability and bioavailability. Computational modeling studies published in 2023 suggest that this molecular architecture allows for optimal interaction with various biological targets, particularly those involving ATP-binding sites in protein kinases.

Recent synthetic methodology developments have significantly improved the production efficiency of 86847-64-5. A 2024 study in the Journal of Medicinal Chemistry reported a novel catalytic system that achieves 92% yield with excellent purity, addressing previous challenges in large-scale synthesis. This advancement has facilitated more extensive biological evaluation of derivatives based on this scaffold.

Pharmacological investigations have identified several N-(3-formyl-2-pyridinyl)-2,2-dimethylpropanamide derivatives showing potent inhibitory activity against JAK kinases, with IC50 values in the low nanomolar range. Particularly noteworthy is its application in developing selective JAK3 inhibitors, which show promise for treating autoimmune disorders while minimizing off-target effects observed with pan-JAK inhibitors.

The compound's metabolic stability has been extensively characterized in recent preclinical studies. Data from 2023-2024 indicate favorable pharmacokinetic properties, including good oral bioavailability (68-72% in rodent models) and moderate plasma protein binding (approximately 85%). These characteristics make it an attractive lead compound for further optimization.

Emerging applications in radiopharmaceutical development have also been reported. Researchers have successfully labeled 86847-64-5 derivatives with fluorine-18 for PET imaging applications, demonstrating specific uptake in inflamed tissues in animal models of rheumatoid arthritis. This dual diagnostic-therapeutic potential represents an exciting new direction for this chemical scaffold.

Ongoing structure-activity relationship studies continue to explore modifications at both the formyl and amide positions. Recent findings suggest that subtle changes in the pivalamide group can dramatically influence target selectivity, opening new possibilities for developing highly specific therapeutic agents with reduced side effect profiles.

Safety evaluations conducted in 2024 indicate that the parent compound shows favorable toxicological parameters, with no significant cytotoxicity observed at therapeutic concentrations in human cell lines. However, researchers caution that certain derivatives may require careful optimization to avoid potential hepatotoxicity observed in some structural analogs.

The pharmaceutical industry has shown growing interest in this compound, with several patents filed in 2023-2024 covering novel synthetic routes and therapeutic applications. This intellectual property activity suggests that 86847-64-5 and its derivatives may soon enter clinical development for various indications, particularly in immunology and oncology.

Future research directions likely will focus on expanding the therapeutic applications of this scaffold, improving synthetic accessibility, and developing more sophisticated prodrug strategies to enhance delivery to specific tissues. The compound's versatility and demonstrated biological activity position it as an important building block in modern drug discovery efforts.

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