Persson, Tobias et al. published their research in Organic & Biomolecular Chemistry in 2007 | CAS: 10199-53-8

1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8) belongs to pyrazole derivatives. Pyrazole has two ring nitrogen atoms in which N1 is pyrrolic and N2 is pyridine-like. The N1 nitrogen is not reactive but is deprotonated in the presence of a base-forming anion. Pyrazole rings have been used as core components of several leading non-steroidal anti-inflammatory drugs (NSAIDs) and antihypertensive drugs. It has also been found to be useful as a bifunctional ligand for metal catalysis.HPLC of Formula: 10199-53-8

Pyrazole carboxamides and carboxylic acids as protein kinase inhibitors in aberrant eukaryotic signal transduction: Induction of growth arrest in MCF-7 cancer cells was written by Persson, Tobias;Yde, Christina W.;Rasmussen, Jakob E.;Rasmussen, Tine L.;Guerra, Barbara;Issinger, Olaf-Georg;Nielsen, John. And the article was included in Organic & Biomolecular Chemistry in 2007.HPLC of Formula: 10199-53-8 This article mentions the following:

Densely functionalized pyrazolecarboxamides, e.g. I, and pyrazolecarboxylic acids were prepared through saponification and transamidation of ester-functionalized pyrazoles. This synthetic protocol allowed for three diversifying steps in which appendages on the pyrazole scaffold were adjusted to optimize inhibition of protein kinases. Thirty-five analogs were tested in CK2, AKT1, PKA, PKCα, and SAPK2a (p38) kinase inhibition bioassays. Blocking of these kinases may lead to effective therapies for treating inflammatory diseases and cancer. In order to investigate potential biol. activity, MCF-7 human breast cancer cells were incubated with the most promising derivatives Two analogs caused changes in MCF-7 cell growth, one of them through cell cycle arrest demonstrated by cell cycle anal. In the experiment, the researchers used many compounds, for example, 1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8HPLC of Formula: 10199-53-8).

1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8) belongs to pyrazole derivatives. Pyrazole has two ring nitrogen atoms in which N1 is pyrrolic and N2 is pyridine-like. The N1 nitrogen is not reactive but is deprotonated in the presence of a base-forming anion. Pyrazole rings have been used as core components of several leading non-steroidal anti-inflammatory drugs (NSAIDs) and antihypertensive drugs. It has also been found to be useful as a bifunctional ligand for metal catalysis.HPLC of Formula: 10199-53-8

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Mitchell, David et al. published their research in Organic Process Research & Development in 2012 | CAS: 141459-53-2

1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine (cas: 141459-53-2) belongs to pyrazole derivatives. Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. Protonation of pyrazole in strong acid leads to pyrazolium cations, which undergo electrophilic substitution preferentially at C3 rather than C4. The pyrazole anion is not reactive toward nucleophiles but is mostly reactive to electrophiles.Reference of 141459-53-2

Development and a Practical Synthesis of the JAK2 Inhibitor LY2784544 was written by Mitchell, David;Cole, Kevin P.;Pollock, Patrick M.;Coppert, David M.;Burkholder, Timothy P.;Clayton, Joshua R.. And the article was included in Organic Process Research & Development in 2012.Reference of 141459-53-2 This article mentions the following:

The route selection and process research and development of a practical synthesis for JAK2 inhibitor LY2784544 is described. The first-generation synthesis route, similar to that used in discovery for derivatization of a benzylic amine moiety, was 14 overall steps and possessed several steps that required extensive development for large-scale production Route selection considerations led to a modified synthesis that utilized a novel vanadium-catalyzed carbon-carbon bond-forming arylation reaction for incorporation of the key benzylic morpholine moiety. A protecting group used to mask an amino pyrazole unit was modified from PMB to tert-Bu, resulting in a dramatic reduction in the overall length of the route. These two major changes resulted in an eight-step synthesis, which was six steps shorter than the first-generation synthesis. In the pilot plant, the new synthesis was scaled to produce >100 kg of LY2784544 in high yield and purity under GMP conditions. The overall development including the vanadium-catalyzed C-C bond-forming methodol., a ketone reductive deoxygenation, and a palladium-catalyzed amination is described. In the experiment, the researchers used many compounds, for example, 1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine (cas: 141459-53-2Reference of 141459-53-2).

1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine (cas: 141459-53-2) belongs to pyrazole derivatives. Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. Protonation of pyrazole in strong acid leads to pyrazolium cations, which undergo electrophilic substitution preferentially at C3 rather than C4. The pyrazole anion is not reactive toward nucleophiles but is mostly reactive to electrophiles.Reference of 141459-53-2

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Laikhter, A. L. et al. published their research in Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya in 1991 | CAS: 5334-39-4

3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4) belongs to pyrazole derivatives. The strategies for the synthesis of pyrazoles generally can be applied for the construction of indazoles. Pyrazole rings have been used as core components of several leading non-steroidal anti-inflammatory drugs (NSAIDs) and antihypertensive drugs. It has also been found to be useful as a bifunctional ligand for metal catalysis.SDS of cas: 5334-39-4

gem-Dinitro compounds in organic synthesis. 2. Synthesis of 4-nitropyrazoles from dinitromethane and its derivatives was written by Laikhter, A. L.;Cherkasova, T. I.;Semenov, V. V.. And the article was included in Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya in 1991.SDS of cas: 5334-39-4 This article mentions the following:

Treating azines RCH:NN:CHR (R = Me, Pr) with the Na salt of CH2(NO2)2 in MeCN gave 27 and 21% nitropyrazoles I. Treating RCH:NN:CHC(NO2)2 K+ in MeCN containing AcOH gave 17 and 18% nitropyrazoles II [R = Me, C(NO2)2], which underwent fluorination and chlorination to give 65 and 81% II [R = C(NO2)2F, C(NO2)2Cl]. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4SDS of cas: 5334-39-4).

3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4) belongs to pyrazole derivatives. The strategies for the synthesis of pyrazoles generally can be applied for the construction of indazoles. Pyrazole rings have been used as core components of several leading non-steroidal anti-inflammatory drugs (NSAIDs) and antihypertensive drugs. It has also been found to be useful as a bifunctional ligand for metal catalysis.SDS of cas: 5334-39-4

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Ahmed, Saleh A. et al. published their research in Photochemical & Photobiological Sciences in 2002 | CAS: 51395-52-9

4-Bromo-3-methyl-1H-pyrazol-5(4H)-one (cas: 51395-52-9) belongs to pyrazole derivatives. Pyrazoles, a five-membered heterocycle containing two adjacent nitrogen atoms, are the core structures found in a number of molecules that possess a wide range of pharmaceutical and agricultural activities. The presence of both electronegative nitrogen atoms in the pyrazole ring reduces the electron density of the C3- and C5-positions leaving electron density of C4-position unaltered. Thus the C4-position is vulnerable to electrophilic attack. The C3 electrophilic-position may undergo deprotonation in the presence of a strong base leading to ring opening.Recommanded Product: 51395-52-9

A highly efficient photochemical bromination as a new method for preparation of mono, bis and fused pyrazole derivatives was written by Ahmed, Saleh A.;Awad, Ibrahim M. A.;Abdel-Wahab, Aboel-Magd A.. And the article was included in Photochemical & Photobiological Sciences in 2002.Recommanded Product: 51395-52-9 This article mentions the following:

N-Bromosuccinimide (NBS) was found to afford photochem. bromination of N-substituted 3-methyl-2-pyrazolin-5-ones in chloroform solution The nature of the products formed was found to be highly dependent on the photolysis time and on the type of N-substituted 3-methyl-2-pyrazolin-5-one. The reaction of substituted 2-pyrazolin-5-ones with NBS in the absence of light yielded in all cases a mixture of N-substituted 3-methyl-4-bromo- (and -4,4-dibromo-) 2-pyrazolin-5-ones. The mechanism of photobromination was illustrated. Separation of all of the products was achieved using column chromatog. The chem. structure of all of the products was assigned by elemental anal., IR, 1H NMR and GC-MS measurements. In the experiment, the researchers used many compounds, for example, 4-Bromo-3-methyl-1H-pyrazol-5(4H)-one (cas: 51395-52-9Recommanded Product: 51395-52-9).

4-Bromo-3-methyl-1H-pyrazol-5(4H)-one (cas: 51395-52-9) belongs to pyrazole derivatives. Pyrazoles, a five-membered heterocycle containing two adjacent nitrogen atoms, are the core structures found in a number of molecules that possess a wide range of pharmaceutical and agricultural activities. The presence of both electronegative nitrogen atoms in the pyrazole ring reduces the electron density of the C3- and C5-positions leaving electron density of C4-position unaltered. Thus the C4-position is vulnerable to electrophilic attack. The C3 electrophilic-position may undergo deprotonation in the presence of a strong base leading to ring opening.Recommanded Product: 51395-52-9

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Shcherbakov, Dmitriy et al. published their research in ACS Medicinal Chemistry Letters in 2022 | CAS: 10199-53-8

1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8) belongs to pyrazole derivatives. Pyrazoles, a five-membered heterocycle containing two adjacent nitrogen atoms, are the core structures found in a number of molecules that possess a wide range of pharmaceutical and agricultural activities. Protonation of pyrazole in strong acid leads to pyrazolium cations, which undergo electrophilic substitution preferentially at C3 rather than C4. The pyrazole anion is not reactive toward nucleophiles but is mostly reactive to electrophiles.Safety of 1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid

Design and Evaluation of Bispidine-Based SARS-CoV-2 Main Protease Inhibitors was written by Shcherbakov, Dmitriy;Baev, Dmitriy;Kalinin, Mikhail;Dalinger, Alexander;Chirkova, Varvara;Belenkaya, Svetlana;Khvostov, Aleksei;Krut’ko, Dmitry;Medved’ko, Aleksei;Volosnikova, Ekaterina;Sharlaeva, Elena;Shanshin, Daniil;Tolstikova, Tatyana;Yarovaya, Olga;Maksyutov, Rinat;Salakhutdinov, Nariman;Vatsadze, Sergey. And the article was included in ACS Medicinal Chemistry Letters in 2022.Safety of 1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid This article mentions the following:

For the first time, derivatives of 3,7-diazabicyclo[3.3.1]nonane (bispidine) were proposed as potential inhibitors of the SARS-CoV-2 main viral protease (3-chymotrypsin-like, 3CLpro). Based on the created pharmacophore model of the active site of the protease, a group of compounds were modeled and tested for activity against 3CLpro. The 3CLpro activity was measured using the fluorogenic substrate Dabcyl-VNSTLQSGLRK(FAM)MA; the efficiency of the proposed approach was confirmed by comparison with literature data for ebselen and disulfiram. The results of the experiments performed with bispidine compounds showed that 14 compounds exhibited activity in the concentration range 1-10μM, and 3 samples exhibited submicromolar activity. The structure-activity relationship studies showed that the mols. containing a carbonyl group in the ninth position of the bicycle exhibited the maximum activity. Based on the exptl. and theor. results obtained, further directions for the development of this topic were proposed. In the experiment, the researchers used many compounds, for example, 1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8Safety of 1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid).

1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8) belongs to pyrazole derivatives. Pyrazoles, a five-membered heterocycle containing two adjacent nitrogen atoms, are the core structures found in a number of molecules that possess a wide range of pharmaceutical and agricultural activities. Protonation of pyrazole in strong acid leads to pyrazolium cations, which undergo electrophilic substitution preferentially at C3 rather than C4. The pyrazole anion is not reactive toward nucleophiles but is mostly reactive to electrophiles.Safety of 1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Wang, Ziyi et al. published their research in Fuel in 2022 | CAS: 141459-53-2

1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine (cas: 141459-53-2) belongs to pyrazole derivatives. Pyrazole is a weak base, with pKb 11.5 (pKa of the conjugated acid 2.49 at 25 °C).Pyrazole used as a ligand to prepare organometallic compounds. Pyrazoles are commonly used scaffold molecules in drug discovery projects. The use of pyrazole derivatives is based on their analgesic, anti-inflammatory, antipyretic, antiarrhythmic, sedative, muscle relaxant, neuroleptic, anticonvulsant, monoamine oxidase inhibitory, antidiabetic and antibacterial activities.Recommanded Product: 1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine

Evolution of S/N containing compounds in pyrolysis of highly oily petroleum sludge was written by Wang, Ziyi;Wang, Zhenbo;Sun, Zhiqian;Ma, Kesheng;Du, Lianmeng;Yuan, Rui. And the article was included in Fuel in 2022.Recommanded Product: 1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine This article mentions the following:

Pyrolysis of oily sludge in inert environment has a strong potential for energy recovery, in which the transformation of S/N containing compounds is a key to influence the quality of various products. This work addresses the evolution of S/N containing compounds in pyrolysis process of two oily sludge samples with high oil content by comparing the species and distribution of S/N containing compounds in origin samples and char. The results demonstrate that aromatic and saturated completed volatilize or react completely at 500 °C while the resin completed the reaction at 750 °C-800 °C. The S-containing compounds are mainly Sulfate-S. At 500 °C, most sulfate remained unchanged, and continued heating led to a large-scale decomposition After condensation and cyclization, the S/N compounds were transformed into components with high thermal stability. Sulfoxide-S, Thiophenic-S and Aromatic-S with more stable thermal stability held the main position at higher temperature The transformation of N-containing compounds was almost based on Proteins-N. As the temperature rising from 500 °C to 700 °C and 900 °C, the content of protein-N decreased continuously and transformed into high thermal stability Pyridine-N, Pyrrole-N and Quaternary graphic-N, which could account for more than 90%. This work provides a theor. basis for the distribution and transformation of S/N in char, the deep application of char and the pollution prevention in subsequent treatment. In the experiment, the researchers used many compounds, for example, 1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine (cas: 141459-53-2Recommanded Product: 1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine).

1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine (cas: 141459-53-2) belongs to pyrazole derivatives. Pyrazole is a weak base, with pKb 11.5 (pKa of the conjugated acid 2.49 at 25 °C).Pyrazole used as a ligand to prepare organometallic compounds. Pyrazoles are commonly used scaffold molecules in drug discovery projects. The use of pyrazole derivatives is based on their analgesic, anti-inflammatory, antipyretic, antiarrhythmic, sedative, muscle relaxant, neuroleptic, anticonvulsant, monoamine oxidase inhibitory, antidiabetic and antibacterial activities.Recommanded Product: 1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Benoit, R. et al. published their research in Synthesis in 1987 | CAS: 3528-58-3

1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3) belongs to pyrazole derivatives. Pyrazoles, a five-membered heterocycle containing two adjacent nitrogen atoms, are the core structures found in a number of molecules that possess a wide range of pharmaceutical and agricultural activities. Pyrazole the presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Category: pyrazoles-derivatives

Facile synthesis of annelated NADH model precursors was written by Benoit, R.;Dupas, G.;Bourguignon, J.;Queguiner, G.. And the article was included in Synthesis in 1987.Category: pyrazoles-derivatives This article mentions the following:

Cyclization of (MeO)2CHC(CN):CHONa I with amino derivatives of electron donating heterocycles II gave 49-85% title compounds III. E.g., the reaction of I with IV gave 49% V. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3Category: pyrazoles-derivatives).

1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3) belongs to pyrazole derivatives. Pyrazoles, a five-membered heterocycle containing two adjacent nitrogen atoms, are the core structures found in a number of molecules that possess a wide range of pharmaceutical and agricultural activities. Pyrazole the presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Category: pyrazoles-derivatives

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Cojocaru, Zenaida et al. published their research in Revista Medicala (Tirgu-Mures, Romania) in 1971 | CAS: 934-48-5

3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. Pyrazole rings have been used as core components of several leading non-steroidal anti-inflammatory drugs (NSAIDs) and antihypertensive drugs. It has also been found to be useful as a bifunctional ligand for metal catalysis.Electric Literature of C6H9N3O

Nitrogeneous five-membered heterocycles. Some pyrazole derivatives with possible hypoglycemic action was written by Cojocaru, Zenaida;Bicleseanu, Cornelia. And the article was included in Revista Medicala (Tirgu-Mures, Romania) in 1971.Electric Literature of C6H9N3O This article mentions the following:

-Acyl-3,5-dimethylpyrazoles (I) were prepared Their phys.-chem. constants were given. The ir spectrum of I showed a carbonyl absorption at 1700-1760 cm-1. The hypoglycemic action of 3,5-dimethylpyrazole and 1-carbamoyl-3,5-dimethyl-pyrazole (I, R = NH2) was compared in rats with that of insulin, sulfamylurea, and biguanidine. In the experiment, the researchers used many compounds, for example, 3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5Electric Literature of C6H9N3O).

3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. Pyrazole rings have been used as core components of several leading non-steroidal anti-inflammatory drugs (NSAIDs) and antihypertensive drugs. It has also been found to be useful as a bifunctional ligand for metal catalysis.Electric Literature of C6H9N3O

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Plate, Ralf et al. published their research in Bioorganic & Medicinal Chemistry in 1996 | CAS: 45887-08-9

3-(1H-Pyrazol-3-yl)pyridine (cas: 45887-08-9) belongs to pyrazole derivatives. As is the case with imidazoles, the pyrazole ring offers many opportunities to create new multiring systems that incorporate this heterocycle. Pyrazoles can be selectively lithiated at different carbons and subsequently react with electrophiles depending on the substitution patterns.Electric Literature of C8H7N3

Synthesis and Muscarinic Activities of 3-(Pyrazolyl)-1,2,5,6-tetrahydropyridine Derivatives was written by Plate, Ralf;Plaum, Marc J. M.;de Boer, Thijs;Andrews, John S.;Rae, Duncan R.;Gibson, Sam. And the article was included in Bioorganic & Medicinal Chemistry in 1996.Electric Literature of C8H7N3 This article mentions the following:

A series of 3-(pyrazolyl)-1,2,5,6-tetrahydropyridine derivatives was synthesized and tested for muscarinic activity in receptor binding assays using [3H]-oxotremorine-M (3H-OXO-M) and [3H]-pirenzepine (3H-PZ) as ligands. Example compounds are the (pyrazolyl)tetrahydropyridines I (R1,R2 = H, halo). Potential muscarinic agonistic or antagonistic properties of the compounds were determined using binding studies measuring their potencies to inhibit the binding of 3H-OXO-M and 3H-PZ. Preferential inhibition of 3H-OXO-M binding was used as an indicator for potential muscarinic agonistic properties: this potential was confirmed in functional studies on isolated organs. All compounds with agonistic properties showed 3H-PZ3H-OXO-M potency ratios in excess of 20. In contrast, for antagonists this ratio was found to be close to unity. Mono-halogenation resulted in compounds with M3 agonistic properties as shown by their atropine sensitive stimulant properties in the guinea pig ileum, but with very little or no M1 activity. Some minor in vivo effects were observed for these compounds One compound also showed pos. mnemonic properties in rats where spatial short-term memory had been compromised by temporary cholinergic depletion. These data indicate that some M3 agonism may be desired in therapeutic agents aimed at the treatment of the cognitive deficits of Alzheimer’s disease patients. In the experiment, the researchers used many compounds, for example, 3-(1H-Pyrazol-3-yl)pyridine (cas: 45887-08-9Electric Literature of C8H7N3).

3-(1H-Pyrazol-3-yl)pyridine (cas: 45887-08-9) belongs to pyrazole derivatives. As is the case with imidazoles, the pyrazole ring offers many opportunities to create new multiring systems that incorporate this heterocycle. Pyrazoles can be selectively lithiated at different carbons and subsequently react with electrophiles depending on the substitution patterns.Electric Literature of C8H7N3

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Sennitskaya, L. V. et al. published their research in Khimiya Geterotsiklicheskikh Soedinenii in 1977 | CAS: 63725-52-0

6-Chloro-1-methylpyrazolo[5,4-b]pyridine (cas: 63725-52-0) belongs to pyrazole derivatives. The 1H-pyrazole provides an excellent means by which to provide the requisite hydrogen bond acceptor–donor motifs, whether as a monocyclic ring or as a fused indazole ring. Pyrazole rings have been used as core components of several leading non-steroidal anti-inflammatory drugs (NSAIDs) and antihypertensive drugs. It has also been found to be useful as a bifunctional ligand for metal catalysis.Product Details of 63725-52-0

IR-spectroscopic study of the structure of indazoles, pyrazolo[3,4-b]pyridines, and pyrazolo[3,4-b]pyrazine was written by Sennitskaya, L. V.;Timoshenkova, Yu. D.;Kikot, B. S.;Pentin, Yu. A.;Blanko, F. F.;Korbukh, I. A.;Preobrazhenskaya, M. N.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1977.Product Details of 63725-52-0 This article mentions the following:

The IR of I (R = H, Me), II, III (R = H, NH2, Me2N), IV, V (R, R1 = H, Me), and VI were discussed. A band at 2500-3300 cm-1, shifted to 2000-2400 cm-1 by deuteration, indicated that intermol. H bonding occurred in the crystals of the NH compounds The IR also indicated that protonation of III (R = NH2) occurred on one of the ring N atoms. In the experiment, the researchers used many compounds, for example, 6-Chloro-1-methylpyrazolo[5,4-b]pyridine (cas: 63725-52-0Product Details of 63725-52-0).

6-Chloro-1-methylpyrazolo[5,4-b]pyridine (cas: 63725-52-0) belongs to pyrazole derivatives. The 1H-pyrazole provides an excellent means by which to provide the requisite hydrogen bond acceptor–donor motifs, whether as a monocyclic ring or as a fused indazole ring. Pyrazole rings have been used as core components of several leading non-steroidal anti-inflammatory drugs (NSAIDs) and antihypertensive drugs. It has also been found to be useful as a bifunctional ligand for metal catalysis.Product Details of 63725-52-0

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics