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Open AccessShort Note

N-(6-Chloro-3-nitropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine

1
Department of Pharmaceutical and Medicinal Chemistry, Institute of Pharmaceutical Sciences, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany
2
Department of Chemistry, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany
3
Cluster of Excellence iFIT (EXC 2180) ‘Image-Guided & Functionally Instructed Tumor Therapies’, Eberhard Karls Universität Tübingen, 72076 Tübingen, Germany
4
Tübingen Center for Academic Drug Discovery, Auf der Morgenstelle 8, 72076 Tübingen, Germany
*
Author to whom correspondence should be addressed.
Molbank 2021, 2021(1), M1181; https://doi.org/10.3390/M1181
Received: 28 December 2020 / Revised: 8 January 2021 / Accepted: 14 January 2021 / Published: 18 January 2021
(This article belongs to the Special Issue Heterocycle Reactions)
Here we describe the synthesis of N-(6-chloro-3-nitropyridin-2-yl)5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine via a three-step procedure including a Buchwald–Hartwig arylamination with benzophenone imine and a highly regioselective nucleophilic aromatic substitution. The title compound was analyzed by nuclear magnetic resonance spectroscopy (1H, 13C, HSQC, HMBC, COSY, DEPT90 and NOESY), high resolution mass spectrometry (ESI-TOF-HRMS) and infrared spectroscopy (ATR-IR) and its structure was confirmed by single crystal X-ray diffraction. The inhibitory potency of the title compound was evaluated for selected kinases harboring a rare cysteine in the hinge region (MPS1, MAPKAPK2 and p70S6Kβ/S6K2). View Full-Text
Keywords: 3-nitropyridines; nucleophilic aromatic substitution; Buchwald–Hartwig arylamination; protein kinase inhibitors; covalent inhibitors 3-nitropyridines; nucleophilic aromatic substitution; Buchwald–Hartwig arylamination; protein kinase inhibitors; covalent inhibitors
MDPI and ACS Style

Wydra, V.; Gerstenecker, S.; Schollmeyer, D.; Andreev, S.; Dimitrov, T.; Massarico Serafim, R.A.; Laufer, S.; Gehringer, M. N-(6-Chloro-3-nitropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine. Molbank 2021, 2021, M1181. https://doi.org/10.3390/M1181

AMA Style

Wydra V, Gerstenecker S, Schollmeyer D, Andreev S, Dimitrov T, Massarico Serafim RA, Laufer S, Gehringer M. N-(6-Chloro-3-nitropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine. Molbank. 2021; 2021(1):M1181. https://doi.org/10.3390/M1181

Chicago/Turabian Style

Wydra, Valentin; Gerstenecker, Stefan; Schollmeyer, Dieter; Andreev, Stanislav; Dimitrov, Teodor; Massarico Serafim, Ricardo A.; Laufer, Stefan; Gehringer, Matthias. 2021. "N-(6-Chloro-3-nitropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine" Molbank 2021, no. 1: M1181. https://doi.org/10.3390/M1181

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