Pyridine-derivatives

Application of 700811-29-6, 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. 700811-29-6, name is 2-Chloro-4-hydrazinopyridine, molecular formula is C5H6ClN3, 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.

To a solution of 1.4 g of (2-Chloro-pyridin-4-yl) -hydrazine (9.79 MMOL, 1.51 equiv) in 30 mL of NMP was added sequentially 2.0 g of N-CYANO-N – (4-ETHOXYCARBONYLPHENYL)-O- phenylisourea (6.45 MMOL, 1.00 equiv) and 10 mL of Hunig’s base. The resulting solution was warmed to 220 C via microwave irradiation for 6 min. The reaction mixture was poured into 100 mL of water and the resulting solid was filtered, yielding 3.0 g of a wet solid, which was dissolved in 40 mL of THF. To the stirred reaction mixture was added 1.50 g of nitrosonium tetrafluoroborate (12.9 MMOL, 2.0 equiv). Rapid bubbling was observed and stirring was continued for 1 hr. 4- [L- (2-CHLORO-PYRIDIN-4-YL)-LH [1, 2,4] TRIAZOL-3-YLAMINO]-BENZOIC acid ethyl ester was filted out of the reaction mixture, yielding 2.0 g (5.83 MMOL, 90.4 % yield) as a yellow SOLID. H NMR (500 MHz, DMSO-d6) 8 10.20 (1 H, s), 9.40 (1 H, s), 8.52 (1 H, d), 8.02 (1 h, s), 7.91 (3 H, m), 7.74 (2 H, d), 7.15 (1 H, br s), 4.27 (2 H, q), 1.31 (3 H, t) ppm. LC/MS : 3.64 min/344.01 (M+1).

According to the analysis of related databases, 700811-29-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; LEDEBOER, Mark W.; DAVIES, Robert J.; WO2005/13982; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 201937-23-7, 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. 201937-23-7, name is 6-Chloronicotinimidamide hydrochloride. A new synthetic method of this compound is introduced below.

2-(6-chloropyridin-3-yl)-N-(l-methyl-lH-pyrazol-4-yl)-4-(propan-2-yloxy)-7,8-dihydropyrido- [4,3-d]pyrimidine-6(5H)-carboxamide (K-2)A mixture of unpurified K-I (12.5 g, 42.5 mmol), 6-chloropyridine-3- carboximidamide hydrochloride (12.2 g, 54.0 mmol), and K2CO3 (17.61 g, 127 mmol) was diluted with DMF (140 ml) and treated with 2-iodopropane (10.62 ml, 106 mmol) in a 1-L round bottom flask with stirring. The reaction mixture was heated to 65 ºC and stirred for 3 h. The mixture was removed from heat and treated with 1.5 L H2O in a 3 -L Erlenmeyer flask to precipitate desired product. The mixture was stirred vigorously for 1 h and filtered through a coarse scintered glass funnel. The wet paste was transferred to a 1-L round bottom flask with toluene (300 mL) and acetone (300 mL) and concentrated in vacuo. The resulting residue was subjected to a second toluene (400 mL) azeotrope. The solids were dried under high vacuum over the weekend. The solids were suspended in 800 mL chloroform and heated to 40 ºC with stirring for 1 hr. The hazy solution was filtered through Celite, and the filtrate was concentrated in vacuo. The resulting off white foam (-12.5 g) was diluted with EtOH (1 L) and stirred at 85 ºC for 1 hr until a clear solution persisted. The solution was cooled RT and concentrated to dryness. The solids were stirred vigorously in Et2O (750 mL) for 15 min, and the mixture was filtered through a large scintered glass funnel. The solids were washed with diethyl ether (3x 350 mL), air-dried under vacuum for 10 min, and then dried under high vacuum for 24 h with routine agitation to afford the title compound (11.5, 63%) as a white solid. Data for K-2: 1H NMR (500 MHz, CDCl3) delta 9.36 (d, J= 1.7, IH), 8.61 (dd, J= 8.3, 2.2 Hz, IH), 7.75 (s, IH), 7.41 (d, J= 8.3 Hz, IH), 7.40 (s, IH), 6.40 (s, IH), 5.60 (hept, J= 6.2 Hz, IH), 4.50 (s, 2H), 3.88 (s, 3H), 3.84 (t, J= 5.6 Hz, 2H), 3.01 (t, J= 5.6 Hz, 2H), 1.46 (d, J= 6.2 Hz, 6H); HRMS m/z (M+H) 424.1561 found, 424.1535 required.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,201937-23-7, its application will become more common.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; BRESLIN, Michael, J.; COLEMAN, Paul, J.; COX, Christopher, D.; RAHEEM, Izzat, T.; SCHREIER, John, D.; WO2010/138430; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 179687-79-7, 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine, 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, Quality Control of 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine, blongs to pyridine-derivatives compound. Quality Control of 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine

EXAMPLE 2 Preparation of 3-chloro-4-(2-pyridylmethoxy)aniline from the nitrobenzene product of Example 1 was accomplished with catalytic hydrogenation using platinum on carbon. A typical hydrogenation was done using 6 volumes of THF, 2% by weight of 5% Pt/C (50% water wet), at 25 psi and at 25-30 C. for approximately 4-6 hours. The reaction is slightly exothermic and the temperature will rise to about 30-35 C. Cooling is necessary to maintain the temperature below 30 C. As a specific example, a mixture of 3-chloro-4-(2-pyridylmethoxy)nitrobenzene (0.15 kg, 0.57 mole) and 2% (w/w) of 5% Pt/C (6.0 g) in tetrahydrofuran (0.90 L) was hydrogenated at 25 psi for at least 5 hours. The mixture was filtered through a celite pad and washed with tetrahydrofuran (0.60 L). The filtrate was distilled to a volume of about 0.75 L and ethanol (1.12 L) was added. Distillation was continued to a volume of about 0.75 L and ethanol (2.85 L) was added. The mixture may be used “as is” in the step of Example 3 below. Performing the hydrogenation in isopropyl alcohol (IPA), methanol (MeOH), or ethanol (EtOH) may result in the product being contaminated with late eluting impurity that partially precipitates out on standing in solution. It was found that performing the hydrogenation in a solvent where both the product and starting material are soluble, such as tetrahydrofuran (THF), resulted in greater product purity and required much less solvent. Thus, THF is a preferred solvent for this step. Experimental results showing the effect of different reaction conditions are shown in Table 2. For the larger scale runs, the first aniline intermediate was not isolated (?NI?) before proceeding with the next step. TABLE 2 Hydrogenation to Form First Aniline Intermediate 5% Scale (g) Pt/C** Solvent Vol Time (h) Yield (%) 2.0 1 IPA 50 3 79.6 18 2.0 5 EtOH 60 3100* 10 1 THF 10 4 94.5 7 10 1 EtOH 10 3 95.6 30 1.05 THF 6.5 12 96.3 14 100 2 THF 6 4.5 97.1 400 2 THF 6 4 NI 500 2 THF 6 4 NI 100 2 THF 6 5 NI 150 2 THF 6 5 NI 7 *Solid impurities noted after reaction completion. **percent by weight of starting material.

The synthetic route of 179687-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; US2006/270668; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 2897-43-0, 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 2897-43-0 as follows.

(C) 2,6-dichloropyridi ne-3,4-diami neTo a solution of 2,6-dichloro-3-nitropyridin-4-amine in ethanol (150 mL) was added iron powder (14.3 g, 0.255 mol), water (46 mL), and then concentrated HCI (28 mL). The reaction mixture was then stirred at 95 C for 16 hours, cooled to roomtemperature, and neutralized. The precipitates were collected by filtration and dried in vacuo. The crude product was then treated with water (200 mL) and extracted with EtOAc (3 x 200 mL). The combined extracts were dried over anhydrous Na2SO4, filtered, and concentrated to afford 7.85 g of the title compound (86.5% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2897-43-0, its application will become more common.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DENG, Wei; JI, Jianguo; WO2012/167733; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1062368-71-1, 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. 1062368-71-1, name is Methyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate, molecular formula is C9H7BrN2O2, 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.

n-Butyllithium (0.251 g, 3.92 mmol, 2.5 M in tetrahydrofuran) and dibutylmagnesium (1.629 g, 11.76 mmol, 1.0 M in heptane) were charged into a nitrogen filled three-necked flask at room temperature. A solution of methyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate (2.000 g, 7.84 mmol) in tetrahydrofuran (25 mL) was added dropwise to the lithium tributylmagnesate complex (n-Bu3MgLi) solution at -25 C. and the mixture was stirred at -10 C. for 1 hour. The resulting mixture was added to a solution of sulfuryl dichloride (1.587 mL, 19.60 mmol) in toluene (20 mL) at -10 C. and the mixture was stirred for 20 minutes at -10 C. The organic solvents were removed by rotary evaporation to give a crude solid. Ammonium hydroxide (15 mL, 7.84 mmol) was added to the crude solid at room temperature, and the mixture was stirred for 15 minutes. After completion, the reaction mixture was concentrated to give crude title product. The crude material was purified by silica gel chromatography (25%-40% ethyl acetated in petroleum) to give crude (75% purity) product. The material was then purified by Prep-HPLC on a Gilson 281(PHG013) with Boston pHlex ODS column (21.2*250 mm, 10 m), using a gradient of acetonitrile (B) and 0.05% trifluoroacetic acid in water (A) at 35-55% B in 10 minute with stop at 15 minute, at a flow rate of 25 mL/minute to provide the title compound. 1H NMR (400 MHz, CDCl3) delta ppm 8.70 (dd, J=6.8, 1.0 Hz, 1H), 8.50 (s, 1H), 8.25 (dd, J=7.4, 1.0 Hz, 1H), 7.08 (t, J=7.1 Hz, 1H), 6.60 (s, 2H), 3.96 (s, 3H). MS (ESI+) m/z 256.1 (M+H)+.

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 1062368-71-1, Methyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Desroy, Nicolas; Gfesser, Gregory A.; Greszler, Stephen N.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Merayo Merayo, Nuria; Pizzonero, Mathieu Rafael; Searle, Xenia B.; Van der Plas, Steven Emiel; Wang, Xueqing; Yeung, Ming C.; Zhao, Gang; (101 pag.)US2018/244640; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6623-21-8, 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 6623-21-8, name is 4,6-Dimethylnicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

4,6-Dimethylnicotinonitrile (1.0 g, 7.6 mmol) was dissolved in ethanol (35 mL) and the mixture was treated with Raney nickel (5 mL, slurry in water) and hydrazine hydrate (3.8 mL, 75.6 mmol). The solution was stirred overnight at room temperature. Compound 2a was obtained by filtering the reaction mixture through a pad of diatomaceous earth, which was rinsed with methanol (3 x 50 ml_). The filtrate was dried over Na2SO4, filtered and concentrated under reduced pressure to afford Compound 2a. The compound was used without additional purification. M+ (ES+) = 137.1 1H NMR (DMSO, d6) delta 2.35 (s, 3H), 2.42 (s, 3H), 4.01 (s, 2H), 7.13 (s, 1H), 8.42 (s, 1 H).

According to the analysis of related databases, 6623-21-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/79214; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1020635-54-4, Adding some certain compound to certain chemical reactions, such as: 1020635-54-4, name is 2-Methoxy-5-nitronicotinic acid,molecular formula is C7H6N2O5, 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 1020635-54-4.

2-Methoxy-5-nitronicotinic acid (36 mmol) and phosphorous pentachloride (72 mmol) were heated at l00C for 2h. The excess reagent was removed in vacuo to give an oily residue.

According to the analysis of related databases, 1020635-54-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIONOMICS LIMITED; O’CONNOR, Sue; RATHJEN, Deborah; (55 pag.)WO2019/109150; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 63237-88-7 ,Some common heterocyclic compound, 63237-88-7, molecular formula is C8H6N2O2, 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: A solution of P(OMe)3 (1.5mmol) in DCM (10mL) was cooled with an ice bath, then I2 (1.5mmol) was added. After the solid iodine was completely dissolved, corresponding acid (1.2mmol) and Et3N (3.0mmol) were added in sequential order, and the solution was stirred for 15min in a cooling bath. Intermediate 5 (1.0mmol) was added and the mixture was stirred for 15min. After removing the cooling bath, the reaction mixture was stirred for 3.5hat room temperature, then diluted with saturated aqueous NaHCO3 and extracted with DCM (10mL) three times. The combined organic layer was sequentially washed with water and brine, dried with anhydrous Na2SO4, and concentrated in vacuo. The crude was purified by column chromatography with DCM/methanol (100:1 to 50:1, v/v) to give the product as a white solid.

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. 63237-88-7, Pyrazolo[1,5-a]pyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Bai, Renren; Shi, Qi; Liang, Zhongxing; Yoon, Younghyoun; Han, Yiran; Feng, Amber; Liu, Shuangping; Oum, Yoonhyeun; Yun, C. Chris; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 464 – 475;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 33630-99-8 , The common heterocyclic compound, 33630-99-8, name is 3-Aminopyridin-2(1H)-one, molecular formula is C5H6N2O, 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.

The amine (64.5 g, 586 mmol , 1.0 Eq) was dissolved in THF (1.6 L) and a solution of Na2CO3 (68.3 g, 644 mmol, 1.1 Eq) in water (800 mL) was added. The reaction was cooled to 0 0C with an ice-bath and benzyl chloroformate (92 mL, 644 mmol, 1.1 Eq) was added drop wise over 30 minutes with vigorous stirring. After addition was complete the reaction was allowed to warm to ambient overnight. The mixture was diluted with water (5 L) and stirred for 30 minutes. The resultant precipitate was removed by filtration. This solid was dissolved in DCM (5 L) with gentle warming and the EPO resultant solution washed with water (2 x 1 L) and brine (1 x 1 L) . The organic layer was dried over Na2SO4 and concentrated in vacuo to give the desired product as a pink solid (120.4 g, 423 mmol, 84%).

The synthetic route of 33630-99-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/27729; (2007); 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 98197-88-7, name is 2-(Hydroxymethyl)-4-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

To cooled solution of oxalyl chloride (0.533 g, 4.18 mmol) in DCM (2mL) at -78 C. under nitrogen was added dimethyl sulfoxide (0.593 mL, 8.37 mmol) dropwise. After 30 minutes (4-nitro-pyridin-2-yl)-methanol (17)(0.129, 0.837 mmol) in DCM (2 mL) was added dropwise maintaining temperature at -78 C. After 2 hours the mixture was warmed to -55 C. Triethylamine (1.74 mL, 12.55 mmol) was then added and the mixture allowed to warm to room temperature over 2 hours. Brine (10 mL) was then added and the mixture extracted with DCM (4*10 mL). The combined organics were then dried over MgSO4 and concentrated in vacuo to an oil. The material was used directly without need for purification assuming quantitative conversion.

With the rapid development of chemical substances, we look forward to future research findings about 98197-88-7.

Reference:
Patent; KuDOS Pharmaceuticals Limited; US2007/93489; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem