175201-95-3

Basic information

• Product Name: 4-CHLORO-1,3-DIMETHYLPYRAZOLO[3,4-B]PYRIDINE-5-CARBONYL CHLORIDE
• Synonyms: BUTTPARK 30\08-35;4-CHLORO-1,3-DIMETHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBONYL CHLORIDE;4-CHLORO-1,3-DIMETHYLPYRAZOLO[3,4-B]PYRIDINE-5-CARBONYL CHLORIDE;4-Chloro-1,3-dimethyl-1H-pyrazol[3,4-b]pyridine-5-carbonyl chloride;4-Chloro-1,3-dimethylpyrazolo[3,4-b]pyridine-5-carbonyl chloride ,97%
• CAS NO: 175201-95-3
• Molecular Formula: C₉H₇Cl₂N₃O
• Molecular Weight: 244.08
• Mol File: 175201-95-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 106℃
• Boiling Point: 365.1°Cat760mmHg
• Flash Point: 174.6°C
• Appearance: /
• Density: 1.57g/cm³
• Vapor Pressure: 1.61E-05mmHg at 25°C
• Refractive Index: 1.682
• CAS DataBase Reference: 4-CHLORO-1,3-DIMETHYLPYRAZOLO[3,4-B]PYRIDINE-5-CARBONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-1,3-DIMETHYLPYRAZOLO[3,4-B]PYRIDINE-5-CARBONYL CHLORIDE(175201-95-3)
• EPA Substance Registry System: 4-CHLORO-1,3-DIMETHYLPYRAZOLO[3,4-B]PYRIDINE-5-CARBONYL CHLORIDE(175201-95-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: 3261
• Hazardous Substances Data: 175201-95-3(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C9H7Cl2N3O/c1-4-6-7(10)5(8(11)15)3-12-9(6)14(2)13-4/h3H,1-2H3

Upstream product

• 175201-94-2 4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid 
• 20481-15-6 ethyl 4-chloro-1,3-dimethylpyrazolo[3,4-b]pyridine-5-carboxylate 
• 20481-33-8 diethyl 2-{[(1,3-dimethyl-1H-pyrazol-5-yl)amino]methylene}malonate 
• 3524-32-1 5-Amino-1,3-dimethylpyrazole 

Downstream Products

• 741290-84-6 ethyl 3-{[5-(aminocarbonyl)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-4-yl]amino}benzoate 
• 741290-75-5 3-{[5-(aminocarbonyl)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-4-yl]amino}benzoic acid 

Relevant articles and documents

A convenient approach to heterocyclic building blocks: Synthesis of novel ring systems containing a [5,6]pyrano[2,3-c]pyrazol-4(1H)-one moiety

Starting from commercially available educts, a straightforward synthetic route to new heterocyclic building blocks is exemplified with the one- or two-step synthesis of tri-, tetra-, or pentacyclic ring systems. Representatives of the following novel ring systems are prepared from 3-methyl-1-phenyl-2- pyrazolin-5-one and the corresponding o-haloarenecarbonyl chloride using calcium hydroxide in refluxing 1,4-dioxane: pyrimidino[4′,5′:5,6]pyrano[2, 3-c]pyrazol-4(1H)-one, thieno[3′,2′:5,6]pyrano[2,3c]pyrazol-4-(1H)- one, thieno[3′,4′:5,6]pyrano[2,3-c]pyrazol-4(1H)-one, thieno[3″,2″:4′,5′]thieno-[2′,3′:5,6] pyrano[2,3-c]pyrazol-4(1H)-one, [1,3]dioxolo[5′,6′][1] benzothieno[2′,3′:5,6]pyrano-[2,3-c]pyrazol-4(1H)-one, pyridazino[4′,3′:5,6]pyrano[2,3-c]pyrazol-4(1H)-one, and pyrazolo[4″,3″:5′,6′]pyrido[3′,4′:5,6] pyrano[2,3-c]pyrazol-6(9H)-one. While the latter two ring systems are directly obtained due to a spontaneous intramolecular substitution reaction, in the other reactions uncyclised 4-aroylpyrazol-5-ols are produced, which are cyclised into the target heterocycles in a subsequent synthetic step (i.e. treatment with NaH in DMF). Detailed NMR spectroscopic investigations (1H-, 13C-, 15N-) with the obtained compounds were undertaken to unambiguously prove the new structures.

Discovery of new orally active phosphodiesterase (PDE4) inhibitors

A series of 4-anilinopyrazolopyridine derivatives were synthesized and biologically evaluated as inhibitors of phosphodiesterase (PDE4). Chemical modification of 3, a structurally new chemical lead that was found in our in-house library, was focused on 1- and 3-substituents. Full details of the discovery of a new orally active chemical lead 5 are presented. Structure-activity relationship data, pharmacological evaluation, and the subtype selectivity study are also presented.