Category: 96630-88-5

Holladay, Mark W.; Bai, Hao; Li, Yihong; Lin, Nan-Horng; Daanen, Jerome F.; Ryther, Keith B.; Wasicak, James T.; Kincaid, John F.; He, Yun; Hettinger, Anne-Marie; Huang, Peggy; Anderson, David J.; Bannon, Anthony W.; Buckley, Michael J.; Campbell, Jeffrey E.; Donnelly-Roberts, Diana L.; Gunther, Karen L.; Kim, David J. B.; Kuntzweiler, Theresa A.; Sullivan, James P.; Decker, Michael W.; Arneric, Stephen P. published the artcile< Structure-activity studies related to ABT-594, a potent nonopioid analgesic agent: effect of pyridine and azetidine ring substitutions on nicotinic acetylcholine receptor binding affinity and analgesic activity in mice>, Application of C5H4ClNO, the main research area is ABT594 analog nonopioid analgesic structure; nicotinic receptor binding ABT594 analog structure.

Analogs of A-98593 (I) and its enantiomer ABT-594 (II) with diverse substituents on the pyridine ring were prepared and tested for affinity to nicotinic acetylcholine receptor binding sites in rat brain and for analgesic activity in the mouse hot plate assay. Numerous types of modifications were consistent with high affinity for [3H]cytisine binding sites. By contrast, only selected modifications resulted in retention of analgesic potency in the same range as I and II. Analogs of II with one or two Me substituents at the 3-position of the azetidine ring also were prepared and substantially less active in both assays.

Bioorganic & Medicinal Chemistry Letters published new progress about Analgesics. 96630-88-5 belongs to class pyridine-derivatives, and the molecular formula is C5H4ClNO, Application of C5H4ClNO.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Voisin, Anne Sophie; Bouillon, Alexandre; Lancelot, Jean-Charles; Rault, Sylvain published the artcile< Efficient synthesis of halohydroxypyridines by hydroxydeboronation>, SDS of cas: 96630-88-5, the main research area is halohydroxypyridine preparation regioselective hydroxydeboronation halopyridinylboronic acid ester.

This paper describes a general method for the synthesis of halohydroxypyridines from novel halopyridinylboronic acids and esters recently described by some of us. Halopyridinylboronic acids and esters have been efficiently hydroxydeboronated under mild conditions by employing hydrogen peroxide or meta-chloroperbenzoic acid. These hydroxylations take place regioselectively without other oxidation (N-oxide formation).

Tetrahedron published new progress about Aromatic nitrogen heterocycles Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 96630-88-5 belongs to class pyridine-derivatives, and the molecular formula is C5H4ClNO, SDS of cas: 96630-88-5.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Matesanz, Encarna; Alcazar, Jesus; Andres, J. Ignacio; Bartolome, Jose M.; De Bruyn, Marcel; Fernandez, Javier; Van Emelen, Kristof published the artcile< Synthesis of novel aza analogues of 2-substituted-2,3-dihydro-1,4-benzodioxins as potential new scaffolds for drug discovery>, Application of C5H4ClNO, the main research area is benzodioxin aza analog preparation.

New synthesis approaches that have led to a series of novel aza analogs of the 2-substituted-2,3-dihydro-1,4-benzodioxin core, bearing versatile bromomethyl group on the non aromatic oxygenated ring, are described. According to their structures these novel scaffolds can be useful intermediates for the preparation of potential new therapeutic agents.

Tetrahedron Letters published new progress about Cyclization, regioselective. 96630-88-5 belongs to class pyridine-derivatives, and the molecular formula is C5H4ClNO, Application of C5H4ClNO.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Zhao, Zean; Liu, Jin; Kuang, Peihua; Luo, Jian; Surineni, Goverdhan; Cen, Xiaolin; Wu, Ting; Cao, Ying; Zhou, Pingzheng; Pang, Jianxin; Zhang, Qun; Chen, Jianjun published the artcile< Discovery of novel verinurad analogs as dual inhibitors of URAT1 and GLUT9 with improved Druggability for the treatment of hyperuricemia>, Recommanded Product: 4-Chloro-3-hydroxypyridine, the main research area is hyperuricemia URAT1 GLUT9 verinurad druggability pharmacokinetics oral bioavailability; Dual inhibitors; GLUT9; URAT1; Verinurad; anti-hyperuricemic.

Verinurad (RDEA3170) is a selective URAT1 inhibitor under investigation for the treatment of gout and hyperuricemia. In an effort to further improve the pharmacodynamics/pharmacokinetics of verinurad and to increase the structural diversity, we designed novel verinurad analogs by introducing a linker (e.g. aminomethyl, amino or oxygen) between the naphthalene and the pyridine ring to increase the flexibility. These compounds were synthesized and tested for their in vitro URAT1-inhibitory activity. Most compounds exhibited potent inhibitory activities against URAT1 with IC50 values ranging from 0.24 μM to 16.35 μM. Among them, compound KPH2f exhibited the highest URAT1-inhibitory activity with IC50 of 0.24 μM, comparable to that of verinurad (IC50 = 0.17 μM). KPH2f also inhibited GLUT9 with an IC50 value of 9.37 ± 7.10 μM, indicating the dual URAT1/GLUT9 targeting capability. In addition, KPH2f showed little effects on OAT1 and ABCG2, and thus was unlikely to cause OAT1/ABCG2-mediated drug-drug interactions and/or to neutralize the uricosuric effects of URAT1/GLUT9 inhibitors. Importantly, KPH2f (10 mg/kg) was equally effective in reducing serum uric acid levels and exhibited higher uricosuric effects in a mice hyperuricemia model, as compared to verinurad (10 mg/kg). Furthermore, KPH2f demonstrated favorable pharmacokinetic properties with an oral bioavailability of 30.13%, clearly better than that of verinurad (21.47%). Moreover, KPH2f presented benign safety profiles without causing hERG toxicity, cytotoxicity in vitro (lower than verinurad), and renal damage in vivo. Collectively, these results suggest that KPH2f represents a novel, safe and effective dual URAT1/GLUT9 inhibitor with improved druggabilities and is worthy of further investigation as an anti-hyperuricemic drug candidate.

European Journal of Medicinal Chemistry published new progress about ATP-binding cassette transporter ABCG2 Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 96630-88-5 belongs to class pyridine-derivatives, and the molecular formula is C5H4ClNO, Recommanded Product: 4-Chloro-3-hydroxypyridine.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Miranda, Margarida S.; Matos, Maria Agostinha R.; Morais, Victor M. F. published the artcile< Structure and energetics correlations in some chlorohydroxypyridines>, COA of Formula: C5H4ClNO, the main research area is chlorohydroxypyridine structure energetics correlation.

We have performed a study of the structure and energetics of some chlorohydroxypyridines based on exptl. calorimetry techniques and high level ab initio computational calculations The standard (p° = 0.1 MPa) molar enthalpies of formation of 2-chloro-3-hydroxypyridine (2-Cl-3-OHPy), 2-chloro-6-hydroxypyridine (2-Cl-6-OHPy) and 3-chloro-5-hydroxypyridine (3-Cl-5-OHPy) in the crystalline phase, at T = 298.15 K, were derived from the resp. standard massic energies of combustion measured by rotating-bomb combustion calorimetry, in oxygen, at T = 298.15 K. The standard molar enthalpies of sublimation, at T = 298.15 K, were measured by Calvet microcalorimetry. From these exptl. determined enthalpic parameters we have derived the standard molar enthalpies of formation of the three compounds in the gaseous phase, at T = 298.15 K: 2-Cl-3-OHPy, -(76.8 ± 2.0) kJ · mol-1; 2-Cl-6-OHPy, -(105.0 ± 1.7) kJ · mol-1, 3-Cl-5-OHPy -(61.2 ± 2.4) kJ · mol-1. These values were compared with estimates obtained from very accurate computational calculations using the G3(MP2)//B3LYP composite method and appropriately chosen reactions. These calculations have also been extended to the remaining chlorohydroxypyridine isomers that were not studied exptl. Based on B3LYP/6-31G* optimized geometries and calculated G3(MP2)//B3LYP absolute enthalpies some structure-energy correlations were discussed.

Journal of Chemical Thermodynamics published new progress about Formation enthalpy (molar). 96630-88-5 belongs to class pyridine-derivatives, and the molecular formula is C5H4ClNO, COA of Formula: C5H4ClNO.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Garrett, Mark D.; Scott, Robin; Sheldrake, Gary N.; Dalton, Howard; Goode, Paul published the artcile< Biotransformation of substituted pyridines with dioxygenase-containing microorganisms>, Product Details of C5H4ClNO, the main research area is toluene dioxygenase substituted pyridine oxidation.

A series of 2-, 3- and 4-substituted pyridines was metabolized using the mutant soil bacterium Pseudomonas putida UV4 which contains a toluene dioxygenase (TDO) enzyme. The regioselectivity of the biotransformation in each case was determined by the position of the substituent. 4-Alkylpyridines were hydroxylated exclusively on the ring to give the corresponding 4-substituted 3-hydroxypyridines, while 3-alkylpyridines were hydroxylated stereoselectively on C-1 of the alkyl group with no evidence of ring hydroxylation. 2-Alkylpyridines gave both ring and side-chain hydroxylation products. Chloro- and bromo-substituted pyridines, and pyridine itself, while being poor substrates for P. putida UV4, were converted to some extent to the corresponding 3-hydroxypyridines. These unoptimized biotransformations are rare examples of the direct enzyme-catalyzed oxidation of pyridine rings and provide a novel synthetic method for the preparation of substituted pyridinols. Evidence for the involvement of the same TDO enzyme in both ring and side-chain hydroxylation pathways was obtained using a recombinant strain of Escherichia coli (pKST11) containing a cloned gene for TDO. The observed stereoselectivity of the side-chain hydroxylation process in P. putida UV4 was complicated by the action of an alc. dehydrogenase enzyme in the organism which slowly leads to epimerization of the initial (R)-alc. bioproducts by dehydrogenation to the corresponding ketones followed by stereoselective reduction to the (S)-alcs.

Organic & Biomolecular Chemistry published new progress about Oxidation, regioselective. 96630-88-5 belongs to class pyridine-derivatives, and the molecular formula is C5H4ClNO, Product Details of C5H4ClNO.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 96630-88-5, 4-Chloro-3-hydroxypyridine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 96630-88-5, blongs to pyridine-derivatives compound. Safety of 4-Chloro-3-hydroxypyridine

This compound was reacted with NaH in DMSO at 50, the reaction mixture cooled and treated with 4-nitrobenzyl bromide for 1 hour. The reaction mixture was worked up with water and ether and the product treated with HCl/ether to give 4-chloro-3-(4-nitrobenzyloxy)pyridine hydrochloride.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,96630-88-5, its application will become more common.

Reference:
Patent; ICI Pharma; US4678781; (1987); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 96630-88-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 96630-88-5, name is 4-Chloro-3-hydroxypyridine, molecular formula is C5H4ClNO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 66 Preparation of (4bR,8aR,9R)-N-(3-(2-(2-methoxyethoxy)ethoxy)pyridin-4-yl)-ll- methyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthren-3-amine (66), hydrochloride salt Step 1. Synthesis of 4-chloro-3-(2-(2-methoxyethoxy)ethoxy)pyridine, A mixture of 4-chloropyridin-3-ol (100 mg, 0.772 mmol), l-bromo-2-(2- methoxyethoxy)ethane (141 mg, 0.772 mmol) and CS2CO3 (503 mg, 1.544 mmol) in dimethylacetamide (5 mL) was irradiated in a microwave at 120 C for two hours. The reaction mixture was cooled to room temperature and poured into 20 mL of water. The aqueous solution was extracted with ethyl acetate 3×20 mL. The organic layer was combined, was washed with brine (50 mL), was dried over anhydrous sodium sulfate, was filtered and was concentrated. The crude product was purified via flash column chromatography on silica gel to afford 4-chloro-3-(2-(2-methoxyethoxy)ethoxy pyridine (87.4 mg, 48.9%). MS (EI) for C10H14CINO3: 232.0 (MH+).

According to the analysis of related databases, 96630-88-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEKTAR THERAPEUTICS; ANAND, Neel; AURRECOECHEA, Natalia; CHENG, Lin; DENG, Bo-liang; O’MAHONY, Donogh; MU, Yongqi; KROGH-JESPERSEN, Erik; (215 pag.)WO2016/182840; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 96630-88-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.96630-88-5, name is 4-Chloro-3-hydroxypyridine, molecular formula is C5H4ClNO, molecular weight is 129.5444, as common compound, the synthetic route is as follows.

a) A solution of diazenedicarboxylic acid diethyl ester (0.1572 mol) in THF (163 ml) was added dropwise to a mixture of 4-chloro-3-pyridinol (0.1429 mol), 2-propen-1-ol (0.1572 mol) and triphenyl-phosphine (0.1572 mol) in THF (276 ml), that was cooled with an ice-water bath and under nitrogen flow.The formed mixture was stirred on the ice-water bath for 15 minutes and at room temperature overnight.The mixture was concentrated under vacuum and the residue was washed with a saturated Na2CO3- solution.The mixture was extracted with DCM and the separated organic layer was dried, filtered and the solvent was evaporated until dry.The residue was treated with DIPE and the formed solid was filtered off and discarded.The filtrate was evaporated until dry and the residue was treated with diethyl ether and the formed solid was filtered off and discarded again.The filtrate was evaporated until dry and the residue was purified by open column chromatography over silica gel (eluent: DCM/2-propanone 99/1;98/2).The product fractions were collected and the solvent was evaporated, yielding 7.9 g of 4-chloro-3-(2-propenyloxy)-pyridine (intermediate (44).

The chemical industry reduces the impact on the environment during synthesis 96630-88-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Van Emelen, Kristof; De Bruyn, Marcel Frans Leopold; Alcazar-Vaca, Manuel Jesus; Andres-Gil, Jose Ignacio; Fernandez-Gadea, Francisco Javier; Matesanz-Ballesteros, Maria Encarnacion; Bartolome-Nebreda, Jose Manuel; US2004/19051; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 96630-88-5, Adding some certain compound to certain chemical reactions, such as: 96630-88-5, name is 4-Chloro-3-hydroxypyridine,molecular formula is C5H4ClNO, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 96630-88-5.

Step A: Preparation of 4-Chloro-3-methoxypyridine. To a cold solution of 4-chloropyridin-3-ol (200 mg, 1.544 mmol), triphenylphosphine (0.810 g, 3.088 mmol), and MeOH (0.125 mL, 3.088 mmol) in THF (5 mL) was slowly added diisopropyl azodicarboxylate (0.610 mL, 3.088 mmol). The reaction was stirred at room temperature for 1 h. The mixture was concentrated under reduced pressure and the residue was triturated with EtOAc to precipitate triphenylphosphine oxide. The solid was removed by filtration and the filtrate was concentrated under reduced pressure and purified by column chromatography to give the title compound (89.4 mg, 0.623 mmol, 40.3%) (purity was about 58 wt%) as a brown oil. LCMS m/z = 144.2 [M+H]+; lU NMR (500 MHz, CDC13) delta ppm 4.00 (s, 3H), 7.32 (d, J = 5.04 Hz, 1H), 8.17 (d, J = 4.41 Hz, 1H), 8.30 (s, 1H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 96630-88-5, 4-Chloro-3-hydroxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert, M.; BUZARD, Daniel, J.; HAN, Sangdon; KIM, Sun, Hee; LEHMANN, Juerg; WO2012/170702; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem