3-nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)-benzenesulfonamide

3-nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)-benzenesulfonamide is a pivotal pharmaceutical intermediate widely recognized as "ABT199 intermediate 2" in the synthesis of Venetoclax (ABT-199), a first-in-class BCL-2 inhibitor approved for chronic lymphocytic leukemia. As a key building block in the Venetoclax synthetic cascade, 3-nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)-benzenesulfonamide provides the essential sulfonamide functionality that contributes to the drug's binding affinity for the BCL-2 protein. 3-nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)-benzenesulfonamide also serves as a reagent for synthesizing BTK, PI3K, and JAK-2 inhibitors, demonstrating the broad applicability of this scaffold in drug discovery. In quality control contexts, 3-nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)-benzenesulfonamide is used as an impurity reference standard (Venclexta Impurity 2) for analytical method development and quality control testing of Venetoclax formulations. The compound is supplied as a yellow to dark yellow solid with a melting point of 188–191°C and purity specifications up to 99.5%. 3-nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)-benzenesulfonamide represents the convergence of synthetic accessibility and biological relevance, making it an indispensable intermediate for pharmaceutical manufacturers and analytical laboratories alike.

Product Parameters

Application

3-nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)-benzenesulfonamide is a reagent used for the synthesis of BTK, PI3K and JAK-2 inhibitors, and is also used as a pharmaceutical intermediate.

Synthetic Route

Dissolve 4-fluoro-3-nitrobenzenesulfonamide (1.0 g, 4.54 mmol), 4-(aminomethyl)tetrahydropyran (0.6 g, 4.49 mmol) and triethylamine (1.3 g, 6.81 mmol) in 10 mL of tetrahydrofuran. After stirring the reaction at room temperature for 5 hours, remove the solvent by distillation under reduced pressure. Add 20 mL of methanol to the residue, and after drying treatment, 1.4 g of 3-nitro-4- (((tetrahydro-2H-pyran-4-yl)methyl)amino) benzenesulfon amide is obtained, with a yield of 97%.

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Whether you are developing Venetoclax manufacturing processes, preparing analytical methods for quality control, or synthesizing novel kinase inhibitors, Cosperpharm is your trusted partner for high-quality intermediates and reference standards. Reach out today to discuss your requirements for 3-nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)-benzenesulfonamide—we look forward to working with you.