Tag: M.W:100-200

Application of 55314-16-4 ,Some common heterocyclic compound, 55314-16-4, molecular formula is C10H12N2O, 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.

176 g (1.00 mol) of starting material III and 121.6 g (1.10 mol) of starting material IV hydrochloride salt wherein R is methyl was added to a solution of 44 g (1.1 mol) of sodium hydroxide in 1000 ml of methanol then stirred and dissolved. The reaction was heated at reflux for 8 hours. The reaction temperature was 65C. After completion of the reaction, the mixture was decolorized at 50C under reduced pressure (i.e., the solvent was removed, the same applies hereinafter). 400 ml of dichloromethane and 400 ml of pure water were further added to dissolve and stir and extract the liquid. The organic layer was washed once more with 400 ml of pure water. 50 g of anhydrous sodium sulfate for 1 hour. Filtered. Solvent was removed to obtain 173.7 g of a pale yellow oil 2-methoxy-4-(3-pyridyl)pyrimidine. The molar yield was 92.8%. HPLC purity 98.72%.

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. 55314-16-4, 1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Peking University Founder Group Co., Ltd.; Southwest Synthetic Pharmaceutical Co., Ltd. of PKU International Healthcare Group Co., Ltd.; PKU Care Pharmaceutical R&D Center Co., Ltd.; PKU Healthcare Industry Group; Xu, Hong; Zhang, Zheng; Wang, Wei; (13 pag.)CN104230885; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 2457-47-8, 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 2457-47-8 as follows.

PREPARATION 27 3,5-Dichloro-4-pyridinecarboxylic acid To a solution of 4.96 ml (0.036 mole) of diisopropylamine in 200 ml of tetrahydrofuran at -65 C. under a nitrogen blanket was added dropwise 14.9 ml of 2.5M n-butyllithium in hexane while maintaining the above temperature. Twenty minutes subsequent to that addition, a solution 5.0 g (0.034 mole) of 3,5-dichloropyridine in 30 ml tetrahydrofuran at -60 to -70 C. was added. The reaction mixture was stirred at -70 C. for 1/2 hr, poured onto a large excess of dry ice and allowed to evaporate overnight at room temperature. The residue was taken up in 100 ml of dilute aqueous sodium hydroxide, washed with 3*30 ml of methylenechloride and filtered. The filtrate was acidified to ~pH 2 with dilute hydrochloric acid to precipitate out the product. After cooling, the precipitate was collected and recrystallized from ethyl acetate/hexane giving 1.9 g (29%) of white analytically pure crystals, m.p. 231-35 C. (decomp.). Analysis: Calculated for C6 H3 NO2 Cl2: C, 37.53; H, 1.57; N, 7.30. Found: C, 37.33; H, 1.56; N, 7.21.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2457-47-8, its application will become more common.

Reference:
Patent; A. H. Robins Company, Inc.; US4705853; (1987); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 134363-45-4 , The common heterocyclic compound, 134363-45-4, name is 2-(Pyridin-3-yl)benzoic acid, molecular formula is C12H9NO2, 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.

Step 3: N-(Benzyloxy)-2-pyridin-3-ylbeiizamide; Ethyl 2-bromobenzoate (380 nag, 1.9 ?rmol), O-hydroxylbenzylamine (280 mg, 2.3 mmol), EDC (440 mg, 2.3 mmol), and HOBT (350 mg, 2.3 mmol) were combined in DMF (2 ml) and stirred over the 2 days at room temperature. The reaction was purified by RP-HPLC (C 18 column; H2CVCH3CN with 0.1% TFA) to afford the title compound. 1H NMR (400 MHz, de-DMSO, ppm): delta 11.6 (s, IH), 8.75 (s, IH), 8.72 (d, J= 4.8 Hz, IH), 8.07 (d, J= 8.0 Hz , IH), 7.73 (t, J= 6.6 Hz, IH), 7.63 (t, J= 7.3 Hz, IH)3 7.57-7.51 (m, 3H), 7.44-7.34 (m, 5H) and 4.76 (s, 2H). ES MS: m/z = 305 (M+l).

The synthetic route of 134363-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2008/10964; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 58584-92-2, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 58584-92-2, name is 2-Amino-6-chloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (4-aminomethyl-phenyl)-phenylamine described in Preparation Example 20 (345mg, 1.74mmol) and 2-amino-6-chloro-nicotinic acid (300mg, 1.74mmol) in N,N-dimethylformamide (10mL) were benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (924mg, 2.09mmol) and triethylamine (0.49mL, 3.48mmol), and the solution was stirred overnight at room temperature. Ethyl acetate and water were added to the reaction solution, which was then partitioned, the organic layer was washed with water, and then, dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by silica gel column chromatography (hexane : ethyl acetate), and the title compound (360mg, 59percent) was obtained as a pale yellow solid. 1H-NMR Spectrum (CDCl3) delta(ppm) : 4.51 (2H, d, J=5.2Hz), 5.74(1 H, s), 6.16(1H, brs), 6.57(1H, d, J=8.0Hz), 6.58(2H, s), 6.94-6.97(1 H, m), 7.04-7.09(4H, m), 7.21-7.30(4H, m), 7.52(1 H, d, J=8.0Hz).

According to the analysis of related databases, 58584-92-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 14150-94-8 , The common heterocyclic compound, 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one, molecular formula is C6H5N3O5, 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.

General procedure: To a solution of dinitropyridone 1 (50.0 mg, 0.25 mmol) in ethanol (5 ml), were added enaminone 4a (38.8 mg, 0.25 mmol) and triethylamine (35mul, 0.25 mmol). The resultant mixture was heated at 100 C for 1 day. After evaporation, the residue was treated with column chromatography on alumina to afford 2-ethanoly-4-nitro-N-propylaniline (3a) (eluted with hexane/ethyl acetate = 8/2, 23.0 mg, 0.11 mmol, 43% (NMR Yield 63%)) as a yellow solid.

The synthetic route of 14150-94-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Naito, Saki; Yokoyama, Soichi; Asahara, Haruyasu; Nishiwaki, Nagatoshi; Tetrahedron Letters; vol. 58; 50; (2017); p. 4699 – 4702;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 22918-01-0, Adding some certain compound to certain chemical reactions, such as: 22918-01-0, name is 2-Bromo-4-chloropyridine,molecular formula is C5H3BrClN, 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 22918-01-0.

Example 103a 2-Bromo-4-chloronicotinaldehyde 103a To a solution of 2-bromo-4-chloropyridine (1.6 g, 8.0 mmol) in anhydrous tetrahydrofuran (40 mL) cooled at -70 C. was added the solution of lithium diisopropyl-amide (5.0 mL, 10.0 mmol, 2.0 M) over a period of 5 minutes and stirred at -70 C. for another 1h. Anhydrous DMF (1.3 g) was introduced over a period of 3 minutes and the mixture was stirred for another 30 minutes. It was then quenched with saturated NH4Cl (30 mL) and extracted with ethyl acetate (20 mL*3). The combined organic layer was dried over anhydrous Mg2SO4, filtered, and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (20:1) to afford 103a as a yellow solid (900 mg, 48%). 1H NMR (500 MHz, DMSO-d6) delta 10.21 (s, 1H), 8.52 (d, J=5.5 Hz, 1H), 7.79 (d, J=5.0 Hz, 1H).

According to the analysis of related databases, 22918-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Wei, BinQing; Young, Wendy B.; US2013/116246; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 139585-48-1, 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. 139585-48-1, name is 2-Chloro-5-methoxypyridine, molecular formula is C6H6ClNO, 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.

Step 2; 2-(5-methoxy-pyridin-2-yl)-benzoic acid diethylamide; Under an argon atmosphere, a mixture of tripotassium phosphate (6.24 g) and water (15 ml) was added to a mixture of 2-chloro-5-methoxy-pyridine (2.05 g), 2-(diethylcarbamoyl)benzeneboronic acid (4.65 g), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride-dichloromethane complex (0.584 g) and toluene (30 ml), and the mixture was stirred at 80 C. for 2 hr. The reaction mixture was cooled to room temperature, water (20 ml), citric acid (2.2 g) and ethyl acetate were added and the mixture was stirred and filtered through celite. The filtrate was partitioned in a separatory funnel. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1 to 1/2) to give a roughly purified product (1.144 g) of the title compound. This product was directly used for the next reaction without further purification.1H-NMR (CDCl3) delta: 8.33 (1H, d, J=2.9 Hz), 7.68 (1H, dd, J=7.7, 1.3 Hz), 7.60 (1H, d, J=8.6 Hz), 7.48-7.32 (3H, m), 7.25-7.15 (1H, m), 3.88 (3H, s), 3.32-2.78 (4H, m), 1.07 (3H, t, J=7.1 Hz), 0.81 (3H, t, J=7.2 Hz).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 139585-48-1, 2-Chloro-5-methoxypyridine.

Reference:
Patent; JAPAN TOBACCO INC.; US2010/240634; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 81719-53-1, Adding some certain compound to certain chemical reactions, such as: 81719-53-1, name is 3,5-Dichloropyridine-2-carboxylic Acid,molecular formula is C6H3Cl2NO2, 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 81719-53-1.

Example B9Preparation of compound 14: rac-3,5-dichloro-pyridine-2-carboxylic acid [3-(4-amino-6- methyl-6,7-dihydro-pyrazolo[l,5-a]pyrazin-6-yl)-4-fluoro-phenyl]-amide and compound 15: (R*)-3,5-dichloro-pyridine-2-carboxylic acid [3-(4-amino-6-methyl- 6,7-dihydro-pyrazolo[l,5-a]pyrazin-6-yl)-4-fluoro-phenyl]-amide and compound 16: (S *)-3 , 5 -dichloro-pyridine-2-carboxylic acid [3 -(4-amino-6-methyl-6, 7-dihydro- pyrazolo[l,5-a]pyrazin-6-yl)-4-fluoro-phenyl]-amide3,5-Dichloro-2-pyridinecarboxylic acid (75.5 mg, 0.393 mmol) was added to a solution of 4-(4,6-dimethoxy-l,3,5-triazin-2-yl)-4-methylmorpholinium chloride (128 mg, 0.463 mmol) in MeOH (5 mL). The mixture was stirred at room temperature for 5 min. Then the mixture was cooled to 0 C and a solution of intermediate A49 (100 mg, 0.386 mmol) in MeOH (5 mL) was added. The mixture was warmed to room temperature and stirred for 4 hours. The mixture was treated with a saturated solution of Na2C03 and H20 and extracted with DCM. The organic layer was separated, dried (MgS04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; MeOH/DCM). The desired fractions were collected and the solvents evaporated in vacuo. The crude product was triturated with Et20, sonicated, filtered and dried in vacuo at 50C. The resulting compound was purified one addition time by flash column chromatography (silica gel; MeOH/DCM) to yield, after treatment with AcOEt and DIPE, compound 14 (95 mg, 57% yield) as a white solid. This racemic compound was then further purified by preparative SFC on Chiralcel OJ-H 5 muiotaeta (250 x 20 mm), mobile phase (0.3% iPr H2, 85% C02, 15% EtOH). The desired fractions for each enantiomer were collected and concentrated in vacuo to yield compound 15 (38 mg, 23% yield). 1H MR (400 MHz, CDC13) delta ppm 1.58 (s, 3 H), 2.52 (br. s., 2 H), 4.41 (br. d, J=13.2 Hz, 1 H), 4.62 (dd, J=13.2, 0.9 Hz, 1 H), 6.43 (d, J=2.1 Hz, 1 H), 7.08 (dd, J=11.7, 8.9 Hz, 1 H), 7.52 (d, J=2.1 Hz, 1 H), 7.81 (dd, J=6.9, 2.8 Hz, 1 H), 7.89 (d, J=2.1 Hz, 1 H), 7.94 (ddd, J=8.8, 4.1, 3.0 Hz, 1 H), 8.42 (d, J=2.1 Hz, 1 H), 9.71 (br. s., 1 H) and compound 16 (40 mg, 24% yield), for which the 1H NMR was in agreement with the one of compound 15.

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. 81719-53-1, 3,5-Dichloropyridine-2-carboxylic Acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; TRABANCO-SUAREZ, Andres, Avelino; GIJSEN, Henricus, Jacobus, Maria; VAN GOOL, Michiel, Luc, Maria; VEGA RAMIRO, Juan, Antonio; DELGADO-JIMENEZ, Francisca; WO2012/117027; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 70165-31-0, name is 6-Cyanonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 70165-31-0

EXAMPLE 1 5-Carboxy-2-(4,5-dihydro-2-thiazolyl)-pyridine Sodium (11 mmol) is added to a flask containing 75 ml of ethanol. As soon as the sodium has dissolved, 10 mmol of 5-carboxy-2-cyanopyridine and 11 mmol of 2-amino-ethanethiol are added and the solution is refluxed for 24 h. The solution is then diluted with 25 ml of water, made acidic (pH=5) with 2N HCl and evaporated. The residue is dissolved in 100 ml of hot chloroform, the salts are filtered off and the filtrate on cooling gives crystals of the title compound, m.p. 234-235 C. The starting material is prepared as follows:

With the rapid development of chemical substances, we look forward to future research findings about 70165-31-0.

Reference:
Patent; Zyma SA; US4904675; (1990); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 10177-29-4, name is 4-Chloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

A 1.0 mol/L borane-tetrahydrofuran complex tetrahydrofuran solution (30 mL) was added to a solution of 4-chloronicotinic acid (1.58 g) in tetrahydrofuran (20 mL), followed by refluxing for 1.5 hours. 2.0 mol/L hydrochloric acid (10 mL) was added thereto, followed by refluxing for 1 hour. The reaction mixture was cooled to room temperature, and extracted with ethyl acetate. The organic layer was washed sequentially with a sodium carbonate aqueous solution and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residues were purified by silica gel column chromatography (ethyl acetate_methanol=1:0?9:1), whereby (4-chloro pyridin-3-yl)methanol (630 mg) was obtained as a white solid. (0954) MS(ESI m/z): 144 (M+H) (0955) RT(min): 0.77

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 10177-29-4, 4-Chloronicotinic acid.

Reference:
Patent; FUJIFILM Corporation; KUBO, Yohei; ANDO, Makoto; TANAKA, Hidehiko; OSAKA, Shuhei; MATSUMOTO, Takuya; NAKATA, Hiyoku; TERADA, Daisuke; NITABARU, Tatsuya; (379 pag.)US2016/168139; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem