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6-Chloro-1H-pyrazolo[4,3-c]pyridine

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6-Chloro-1H-pyrazolo[4,3-c]pyridine Basic information
Product Name:6-Chloro-1H-pyrazolo[4,3-c]pyridine
Synonyms:6-Chloro-1H-pyrazolo[4,3-c]pyridine;1H-Pyrazolo[4,3-c]pyridine, 6-chloro-;6-Chloro-5-azaindazole;6-Chloro-1H-Pyrazolo[4,3-C]Pyridine(WXC01805);100587;6-chloro-1H-pyrazolo[4,4-c]pyridine;6-Chloro-1H-pyrazolo[4,3-c]pyridine;6-chloro-pyrazolo[4,3-c]pyridine
CAS:1206979-33-0
MF:C6H4ClN3
MW:153.57
EINECS:
Product Categories:
Mol File:1206979-33-0.mol
6-Chloro-1H-pyrazolo[4,3-c]pyridine Structure
6-Chloro-1H-pyrazolo[4,3-c]pyridine Chemical Properties
Boiling point 358℃
density 1.531
Fp 201℃
storage temp. Keep in dark place,Sealed in dry,Room Temperature
form powder
pka10.46±0.40(Predicted)
color Yellow
InChIInChI=1S/C6H4ClN3/c7-6-1-5-4(2-8-6)3-9-10-5/h1-3H,(H,9,10)
InChIKeyAAJIQIWPVIWCGA-UHFFFAOYSA-N
SMILESC1=NC(Cl)=CC2NN=CC1=2
CAS DataBase Reference1206979-33-0
Safety Information
Hazard Codes Xn
Risk Statements 22
WGK Germany 3
HS Code 2933790090
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
MSDS Information
6-Chloro-1H-pyrazolo[4,3-c]pyridine Usage And Synthesis
UsesUsed as a pharmaceutical intermediate for laboratory research and development.
General Description6-Chloro-1H-pyrazolo[4,3-c]pyridine is the key starting material for the synthesis of 1-(1H-pyrazolo[4,3-c]pyridin-6-yl)urea ERK inhibitors. By iodinating the C-3 position and protecting the N-1 position with a triphenylmethyl group, it can be used to prepare 6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridine[5].
Synthesis4,6-Dichloropyridine-3-carbaldehyde (3.7 g, 32 mmol), hydrazine (3.5 mL, 110 mmol) and N,N-diisopropylethylamine (20 mL) were combined in DMA (100 mL) and stirred at 80° C. for four hours. Then, the solution was cooled to room temperature, diluted with EtOAc, and washed three times with water and then with brine. The organic solution was concentrated and the resulting mixture was precipitated from dichloromethane to give 6-chloro-1H-pyrazolo[4,3-c]pyridine. Yield 2 g (41%). LCMS (ESI): calc. C6H4ClN3=153; obs. M+H=154.
6-Chloro-1H-pyrazolo[4,3-c]pyridine synthesis
References[1] Patent: WO2015/38417,  2015,  A1. Location in patent: Page/Page column 78
[2] Patent: WO2013/169704,  2013,  A2. Location in patent: Paragraph 0232
[3] Patent: WO2014/210354,  2014,  A1. Location in patent: Page/Page column 41
[4] Bioorganic and Medicinal Chemistry Letters,  2008,  vol. 18,  # 20,  p. 5648 - 5652
[5] Lim*, J., Kelley, E. H., Methot, J. L. (2016). Discovery of 1-(1H-Pyrazolo[4,3-c]pyridin-6-yl)urea Inhibitors of Extracellular Signal-Regulated Kinase (ERK) for the Treatment of Cancers. Journal of Medicinal Chemistry, 59 13, 6501–6511. https://doi.org/10.1021/acs.jmedchem.6b00708
Tag:6-Chloro-1H-pyrazolo[4,3-c]pyridine(1206979-33-0) Related Product Information
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