Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 1008-91-9, 1-(Pyridin-4-yl)piperazine, 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, Computed Properties of C9H13N3, blongs to pyridine-derivatives compound. Computed Properties of C9H13N3

The crude material (1.15 g, 7.06 mmol) from Step B was dissolved in dichloromethane (50 mL). After addition of diisopropylethylamine (4.7 mL, 42.4 mmol), 3-nitrosali-cylic acid (1.94 g, 10.6 mmol), and PyBrOP (5.78 g, 12.3 mmol), the resulting mixture was stirred over night at room temperature before being put into IN sodium hydroxide (300 mL). Extraction with dichloromethane (2×100 mL) removed all PyBrOP products. The aqueous phase was carefully acidified to pH~5-6 with 3N HC1 and extracted with dichloromethane (3×100 mL). The combined organic layers of the neutral extraction were dried over sodium sulfate, concentrated, and finally purified by column chromatography (dichloromethane/methanol/NH4OH=10/l/0.1) to yield the desired product (850 mg, 37% for 2 steps).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1008-91-9, 1-(Pyridin-4-yl)piperazine, and friends who are interested can also refer to it.

Reference:
Patent; Schering Corporation and Pharmacopeia, Inc.; US2004/147559; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 107504-08-5, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 107504-08-5, name is 5-Fluoro-2-picolinic acid. A new synthetic method of this compound is introduced below.

General procedure: 5-fluoropicolinic acid (8.0 g, 56.7 mmol) was dissolved in methanol (50 mL),Dichlorosulfoxide (13.5 g, 113.4 mmol) was added, heated to 70 C. for 16 hours, and concentrated, and the residue was used directly in the next step. (8.0g, yield: 90.9%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,107504-08-5, its application will become more common.

Reference:
Patent; Shandong Xuanzhu Pharmaceutical Technology Co., Ltd.; Wang Tingzhong; Liu Bin; (31 pag.)CN110698471; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 15128-82-2 ,Some common heterocyclic compound, 15128-82-2, molecular formula is C5H4N2O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

(S)-1-(2,6-dichloro-3-fluorophenyl)ethanol (20.9 g, 0.10 mol) was dissolved in 200 mL anhydrous tetrahydofuran, to which 3-hydroxy-2-nitropyridine (16.0 g, 0.11 mol) and triphenylphosphine (40.0 g, 0.15 mol) were sequentially added under a nitrogen atmosphere, and the reaction solution was stirred at room temperature for 1 hour, cooled to 0 C. and diisopropyl azodicarboxylate (40 mL, 0.15 mol) was added dropwise. After the addition was complete, stirring was continued at 0 C. for 12 hours. The solvent was distilled off to obtain an oily material, which was separated by silica gel column chromatography, to give (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine (20.2 g). Yield: 61%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,15128-82-2, its application will become more common.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; LIANYUNGANG RUNZHONG PHARMACEUTICAL CO., LTD.; CENTAURUS BIOPHARMA CO., LTD.; GONG, Feng; LI, Xinlu; ZHAO, Rui; ZHANG, Xiquan; XU, Xinhe; LIU, Xijie; XIAO, Dengming; HAN, Yongxin; (22 pag.)US2018/244649; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 186593-43-1, Adding some certain compound to certain chemical reactions, such as: 186593-43-1, name is 5-Amino-3-bromo-2-methylpyridine,molecular formula is C6H7BrN2, 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 186593-43-1.

General procedure: 1.2.2.1. General method Bl To a stirred solution of Intermediate Gen-1 (1 to 1.2 eq.), and amine derivative (1 eq.) in DCM or DMF are added TBTU or HATU (1 to 1.2 eq.) followed by TEA or NMM (2 to 3 eq.) at room temperature under argon, the reaction mixture is stirred at room temperature until completion. Then the reaction is quenched with water, the layers are separated. The organic layer is dried over Na2SO i, filtered and evaporated to dryness. Alternatively, the reaction is concentrated in vacuo, the residue is partionned between EtOAc or a mixture of EtOAc/nBuOH and a saturated aqueous NH4C1 solution or water. The layers are separated, the organic layer is dried over Na2S04, filtered and evaporated to dryness. Then the residue is purified by chromatography on silica gel to afford the expected Intermediate.

According to the analysis of related databases, 186593-43-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALAPAGOS NV; SANIERE, Laurent Raymond Maurice; HUCK, Jacques; DYKES, Graeme James; SCHMITT, Benoit Antoine; BLANC, Javier; BUTLER, Anna Sara; BEAUMONT, Stephane Nicolas Alain; BONNATERRE, Florence Marie-Emilie; WO2015/24905; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 500-22-1, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 500-22-1 as follows.

General procedure: In a round-bottomed flask equipped with a condenser and a magnetic stirrer, a mixture of aldehyde (1 mmol), 1,2-phenylenediamine (1 mmol) and Cu(II)-TDnSiO2 (10 mg, containing 0.0034 mmol Cu(II)) in EtOAc (2 mL) was stirred at 50 C. The progress of the reaction was monitored by TLC (eluent: n-hexane/EtOAc, 2:1). After completion of the reaction, the mixture was cooled to room temperature and EtOAc/EtOH (3:2, 15 mL) was added. The catalyst was separated by filtration and washed with EtOAc (10 mL). The filtrate was evaporated and the crude product was purified by recrystallization from EtOAc or EtOH to afford the pure product

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,500-22-1, its application will become more common.

Reference:
Article; Nasr-Esfahani, Mahboobeh; Mohammadpoor-Baltork, Iraj; Khosropour, Ahmad Reza; Moghadam, Majid; Mirkhani, Valiollah; Tangestaninejad, Shahram; Journal of Molecular Catalysis A: Chemical; vol. 379; (2013); p. 243 – 254;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1620-77-5, 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.1620-77-5, name is 5-Methylpicolinonitrile, molecular formula is C7H6N2, molecular weight is 118.14, as common compound, the synthetic route is as follows.

[5-METHYL-PYRIDINE-2-CARBONITRILE] (3.34 g, 28.3 mmol) was mixed with [18] percent HCl (12 ml) and ethanol [(6ML)] and refluxed for 40 h. The reaction mixture was concentrated by rotavapor and the residue was triturated with acetone to give off-white solid 5-methyl-pyridine-2- carboxylic acid hydrochloride. This solid was hydrogenated with [PT02] in ethanol for 2 days until no W active material left. The reaction mixture was filtered, concentrated by vacuum. The residue was triturated with acetone to give 5.3 g of cis and trans 5-methyl- piperidine-2-carboxylic acid hydrochloride as white solid (quantitative).

Statistics shows that 1620-77-5 is playing an increasingly important role. we look forward to future research findings about 5-Methylpicolinonitrile.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2004/14902; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 76469-41-5, 2,3,5-Trifluoropyridine, 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, 76469-41-5, blongs to pyridine-derivatives compound. Formula: C5H2F3N

A mixture of 2, 3, 5-trifluoropyridine (5.0 g, 37.6 mmol, 1.0 equiv) and 1, 3-dimethyl propanedioate (7.4 g, 56.0 mmol, 1.5 equiv) and Cs 2CO 3 (24.5 g, 75.2 mmol, 2.0 equiv) in DMSO (100.0 mL) was stirred for 10 hours at 100C under nitrogen atmosphere. The resulting mixture was extracted with EtOAc (4 x 50 mL). The combined organic layers were washed with H2O (3 x 50 mL), dried over anhydrous Na 2SO 4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with PE/EtOAc (20: 1) to afford 1, 3-dimethyl 2- (3, 5-difluoropyridin-2-yl) propanedioate (8.1 g, 79.13%) as a yellow oil. LCMS: m/z (ESI), [M+H] + = 246.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,76469-41-5, its application will become more common.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD.; ZENG, Qingbei; QI, Changhe; TSUI, Honchung; YANG, Zhenfan; ZHANG, Xiaolin; (206 pag.)WO2020/52631; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 55314-16-4, 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.55314-16-4, name is 1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one, molecular formula is C10H12N2O, molecular weight is 176.2151, as common compound, the synthetic route is as follows.

The starting material was added 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one (Compound 4) (1.76 g, 0.01 mol) in a three-neck flask.Guanidine hydrochloride (2.87 g, 0.03 mol)And sodium hydroxide (1.2g, 0.03mol), add 25ml of solvent t-butanol, stir, heated in a constant temperature oil bath to 85 C reflux reaction, 6-8h. After the reaction is completed, the solvent is spin-dried, an appropriate amount of water and ethyl acetate are added, the insoluble solid is filtered, and the filter cake is washed with water and dried to obtain a yellow solid; the filtrate is further subjected to extraction, the organic phase is collected, dried, and the solvent is dried and dried. The solid was subjected to column chromatography to give a pale yellow solid, Compound 5 (1.55 g, yield: 90%).

Statistics shows that 55314-16-4 is playing an increasingly important role. we look forward to future research findings about 1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one.

Reference:
Patent; Southeast University; Cai Jin; Ning Yao; Ji Min; Wang Yingying; Huang Mingqi; (20 pag.)CN110078708; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1093880-37-5, Adding some certain compound to certain chemical reactions, such as: 1093880-37-5, name is 6-Chloro-2-fluoronicotinaldehyde,molecular formula is C6H3ClFNO, 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 1093880-37-5.

Example 112A methyl 3 -(3 -(6-chloro-2-fluoropyridin-3 -yl)-3 -hydroxypropanoyl)benzoate A solution of methyl 3-acetylbenzoate (1 g, 5.61 mmol) in tetrahydrofuran (25 mL) was cooled to – 78 C, treated dropwise with 1 M lithium bis(trimethylsilyl)amide in tetrahydrofuran (7.30 ml, 7.30 mmol), stirred at – 78 C for 15 minutes, treated dropwise with a solution of 6- chloro-2-fluoronicotinaldehyde (0.895 g, 5.61 mmol) in tetrahydrofuran (10 mL), stirred at -78 C for 15 minutes, treated with saturated NH4C1 solution (30 mL) and the mixture was allowed to warm to near room temperature. The mixture was extracted with ethyl acetate (30 mL) and the layers were separated. The aqueous layer was extracted with ethyl acetate (20 mL). The combined organic layers were washed with brine, dried (MgS04), filtered, and concentrated. The residue was chromatographed on silica gel and eluted with a gradient of 20 % – 100 % ethyl acetate in heptanes to provide the title compound (1.35 g, 4.00 mmol, 71.2 % yield). 1H NMR (400 MHz, CDCl3) 5 ppm 8.56 (t, J = 1.8 Hz, 1H), 8.28 (dt, J= 7.7, 1.5 Hz, 1H), 8.15 (dt, J = 7.9, 1.6 Hz, 1H), 8.10 – 8.05 (m, 1H), 7.59 (t, J = 7.8 Hz, 1H), 7.30 (dd, J= 7.8, 1.0 Hz, 1H), 5.53 (dt, J= 9.4, 2.9 Hz, 1H), 3.96 (s, 3H), 3.89 (d, J= 3.9 Hz, 1H), 3.55 (dd, J= 18.0, 2.4 Hz, 1H), 3.29 (dd, J= 18.0, 9.3 Hz, 1H); MS (ESI) m/z 338 (M+H)+.

According to the analysis of related databases, 1093880-37-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBVIE INC.; KYM, Philip, R.; WANG, Xueqing; SEARLE, Xenia, B.; LIU, Bo; YEUNG, Ming, C.; ALTENBACH, Robert, J.; VOIGHT, Eric; BOGDAN, Andrew; KOENIG, John, R.; (332 pag.)WO2016/69757; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 72990-37-5 , The common heterocyclic compound, 72990-37-5, name is 3-Chloroisonicotinaldehyde, molecular formula is C6H4ClNO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a solution of 3-chloropyridine-4-carbaldehyde (3.58 g, 25.3 mmol) in MeOH(150 mL) at 0 C was added NaBH4 (1.91 g, 50.6 mmol) portion wise. The mixture was stirred at this temperature for 5 min then allowed to warm up to rt and stirred at this temperature for 1.5 h. The reaction mixture was quenched with saturated aqueous solution of NH4Cl. Volatiles were removed in vacuo and the aqueous layer was extracted with EtOAc (150 mL). The organic layer was washed successively with water (150 mL) and brine (150 mL), dried over Na2SO4, filtered and concentrated in vacuo to give chloropyridine 33 (3.58 g, 99%) as a white solid which was used in the next step without further purification.

The synthetic route of 72990-37-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jepsen, Tue Heesgaard; Glibstrup, Emil; Crestey, Francois; Jensen, Anders A.; Kristensen, Jesper Langgaard; Beilstein Journal of Organic Chemistry; vol. 13; (2017); p. 988 – 994;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem