Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 1824-81-3, 2-Amino-6-picoline, 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, HPLC of Formula: C6H8N2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H8N2

(1) 200 mL of acetic anhydride was added to 39.9 g of 2-amino-6-methylpyridine at room temperature, and the mixture was stirred at 70C for 2 hours. The obtained reaction solution was concentrated, neutralized with an aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The organic phase was washed with saturated brine. Subsequently, the organic phase was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated to obtain 60.6 g of an acetamide product [149-1] as follows. [Show Image] The spectral data of the compound represented by the above Formula [149-1] is presented below. 1H-NMR (CDCl3) delta: 8.10 (1H, brs), 7.97 (1H, d, J=8.0 Hz), 7.57 (1H, t, J=8.0 Hz), 6.88 (1H, d, J=8.0 Hz), 2.43 (3H, s), 2.17 (3H, s). mass: 151 (M+1)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1824-81-3, 2-Amino-6-picoline, and friends who are interested can also refer to it.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1754706; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6980-08-1 , The common heterocyclic compound, 6980-08-1, name is 4-Chloro-3-nitropyridin-2-amine, molecular formula is C5H4ClN3O2, 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.

a) Diethyl 2-(2-amino-3-nitropyridin-4-yl)malonate (A 132) NaH (60% dispersion in mineral oil, 0.830 g, 20.7 mmol) was added to a solution of diethyl malonate (3.16 ml_, 20.7 mmol) in NMP (50 ml_) and the resulting solution was stirred at room temperature for 10 minutes. 4-Chloro-3-nitropyridin-2-amine A14 (1.00 g, 5.76 mmol) was then added and the mixture heated at 50 C for 2 hours. The mixture was cooled to room temperature and diluted with EtOAc (250 ml_) and water (100 ml_). The organic layer was separated and washed with water (100 ml_) followed by brine (100 ml_). This process was repeated three times before the organic layer was dried (Na2S04), filtered and the filtrate concentrated under reduced pressure to give a yellow oil which was purified by silica gel column chromatography (40 g Si02 cartridge, 0-100% EtOAc in petroleum benzine 40-60 C) to give the title compound as a yellow solid (1.69 g, 99%). H NMR (400 MHz, ck-DMSO) delta 8.28 (d, J = 4.9 Hz, 1 H), 7.53 (s, 2H), 6.58 (d, J = 5.0 Hz, 1 H), 5.20 (s, 1 H), 4.18 (qd, J = 7.1 , 0.9 Hz, 4H), 1.18 (t, J = 7.1 Hz, 6H). LCMS-B: rt 3.20 min, m/z (positive ion) 298 [M+H]+.

The synthetic route of 6980-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LTD; STUPPLE, Paul Anthony; WALKER, Scott Raymond; PINSON, Jo-Anne; LAGIAKOS, Helen Rachel; LUNNISS, Gillian Elizabeth; HOLMES, Ian Peter; STUPPLE, Alexandra Elizabeth; BERGMAN, Ylva Elisabet; FOITZIK, Richard Charles; KERSTEN, Wilhelmus Johannes Antonius; CAMERINO, Michelle Ang; WO2014/128465; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 7584-05-6, Adding some certain compound to certain chemical reactions, such as: 7584-05-6, name is 3-Methylisonicotinonitrile,molecular formula is C7H6N2, 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 7584-05-6.

To a stirred solution of 3-methylisonicotinonitrile (5.00 g, 42.30 mmol) in DCM(100 mL)was added 3chioroperoxybenzoic acid (14.61 g, 85.00 nimol) at 0 C and stirred at ambienttemperature for 16 h. The reaction mixture was diluted with water (50 mL), basified with 10 % NaHCO3 and extracted with ethyl acetate (2 x 75 mL). The combined organic layers were washed with brine (50 mL), dried over sodium sulfate and evaporated under reduced pressure to obtain Intermediate 24A (3.50 g, 61.30%) as a pale yellow solid. ?HNIVR (400 MHz, DMSOd6) oe ppm 2.38 (s, 3 H), 7.84 7.85 (d, .1= 6.8 Hz, 1 H), 8.21 8.23 (dd, J= 1.2 Hz, 6.8 Hz, IH),8.41 (s, 1H). LCMS MethodD): retention time 0.44 mm, [M+H1 135.2.

According to the analysis of related databases, 7584-05-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; PANDA, Manoranjan; YADAV, Navnath Dnyanoba; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (321 pag.)WO2018/93569; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 54221-95-3, name is 2-Acetylaminoisonicotinic acid. A new synthetic method of this compound is introduced below., Product Details of 54221-95-3

(C) Ethyl 2-aminoisonicotinate 2-(Acetylamino)isonicotinic acid (13 g, 73.60 mmol) synthesised by the method of Example 7, (A) was added with ethanol (50 ml) and toluene (150 ml) and heated to 100-110 C. The mixture was added dropwise with concentrated sulfuric acid (7 ml) and heated for 11 hour with stirring. The reaction solution was returned to room temperature and poured into saturated aqueous sodium hydrogencarbonate cooled with ice. The mixture was extracted with chloroform and the collected organic layer was dried over magnesium sulfate and concentrated under reduced pressure to obtain 7.6 g (23% for the two steps) of the title compound as pale yellow crystals without purification. 1H-NMR (CDCl3) delta: 1.39 (3H, t, J=7.07 Hz), 4.37 (2H, qu, J=7.07 Hz), 4.63 (2H, brd), 7.07 (1H, s), 7.17 (1H, dd, J=0.98, 5.12 Hz), 8.18 (1H, d, J=5.12 Hz) EI/MS; m/z: 165 (M+-1)

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, 54221-95-3, 2-Acetylaminoisonicotinic acid.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD; US2003/92720; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.24484-93-3, name is Methyl 4-chloropicolinate, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.Computed Properties of C7H6ClNO2

(Production Example 22) 4-(4-Amino-2-fluorophenoxy)pyridine-2-carboxylic acid methyl ester dihydrochloride 4-Chloropyridine-2-carboxylic acid methyl ester (30 g) and 2-fluoro-4-nitrophenol (41.2 g) were dissolved in chlorobenzene (24 ml), followed by stirring under a nitrogen atmosphere at 120 C for 4 hr. The reaction mixture was allowed to cool down to room temperature, methanol (100 ml) was added, and stirred for 30 min. The solvent was removed under reduced pressure, then the resultant residue was partitioned between ethyl acetate (300 ml) and a 1N aqueous solution of sodium hydroxide (150 ml). The separated organic layer was washed with a 1N aqueous solution of sodium hydroxide (100 ml) and brine (150 ml) and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, ethanol (200 ml) was added to the resultant residue, followed by stirring for 30 min. The solid was collected by filtration and the filtrate was purified by silica gel column chromatography (YMC, SIL-60-400/230W, eluent; heptane:ethyl acetate = 1:1). Fractions containing the target compound were concentrated under reduced pressure, the resultant solid was combined to the solid above to provide 4-(2-fluoro-4-nitrophenoxy)pyridine-2-carboxylic acid methyl ester as a pale brown solid (20.0 g, 40.0 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,24484-93-3, Methyl 4-chloropicolinate, and friends who are interested can also refer to it.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP1889836; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 791644-48-9, 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 791644-48-9 as follows.

5-Fluoro-lH-pyrazolo [3, 4-b]pyridin-3-amine (5) [00148] To a solution of compound 4 (50 g, 321.7 mmol) in 1-butanol (1 L) was added hydrazine monohydrate (150 mL, 3.2 mol) , and the mixture was refluxed for 4 h. The mixture was cooled to room temperature and concentrated. The precipitate was successively washed on filter with water (2x) and Et2<0 (2x) and dried in vacuo overnight to give compound 5 (44 g, 88percent) as a yellow solid. 1H NMR (DMSO-d6, 300 MHz): delta 5.53 (s, 2H); 7.94 (dd, IH); 8.35 (dd, IH); 12.02 (s, IH). These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,791644-48-9, its application will become more common. Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/112646; (2008); 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 73027-79-9, name is 4,6-Dichloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Safety of 4,6-Dichloronicotinic acid

To a solution of 4,6-dichloronicotinic acid (250 mg, 1.302 mmol), ethyl 3- aminopropanoate hydrochloride (210 mg, 1.367 mmol) and pyridine (0.263 mL, 3.26mmol) in DCM (5 mL) at 0 C was added phosphoryl trichloride (319 mg, 2.083 mmol). The mixture was stirred at room temperature for 2 hrs. The reaction mixture was poured into iced water, extracted with DCM (50 mL), washed with saturated NaHCO3 (aq) and brine. The organic extract was dried over Na2SO4, filtered and concentrated in vacuo. The crude intermediate, ethyl 3-(4,6-dichloronicotinamido)propanoate, was thendissolved in dry THF (5 mL) and put under an atmosphere of nitrogen. The solution obtained was cooled to 0 C. Methylmagnesium bromide (2.60 mL, 7.81 mmol) was added and the mixture was stirred at room temperature for 3h. The reaction mixture was quenched with a saturated solution of NH4C1 (aq), extracted with ethyl acetate, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crudeintermediate 4,6-dichloro-N-(3 -hydroxy-3-methylbutyl)nicotinamide was dissolved in DCM (5 mL) and the mixture was cooled to 0 C. DAST (0.189 mL, 1.432 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was then quenched with a saturated solution of NaHCO3 (aq), extracted with DCM, dried over Na2SO4, filtered and concentrated in vacuo. The cmde product was purified viacolumn chromatography to afford 4,6-dichloro-N-(3-fluoro-3-methylbutyl)nicotinamide(126 mg, 35 % yield). LCMS m/z 279.2 (M+H) ?H NMR (400MHz, CDC13) 8.67 (s,1H), 7.48-7.38 (m, 1H), 6.70-6.50 (m, 1H), 3.74-3.59 (m, 2H), 2.06-1.90 (m, 2H), 1.48 (s,3H), 1.43-1.42 (m, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 73027-79-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DUNCIA, John V.; GARDNER, Daniel S.; HYNES, John; MACOR, John E.; MURUGESAN, Natessan; SANTELLA, Joseph B.; WU, Hong; KANTHETI, Durgarao; NAIR, Satheesh Kesavan; PAIDI, Venkatram Reddy; RATNA KUMAR, Sreekantha; SARKUNAM, Kandhasamy; SISTLA, Ramesh Kumar; POLIMERA, Subba Rao; (254 pag.)WO2016/210036; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 18614-51-2, name is 4-Amino-2-fluoropyridine, the common compound, a new synthetic route is introduced below. Quality Control of 4-Amino-2-fluoropyridine

In a 10 mL microwave vial, Pd2(dba)3 (21.61 mg, 0.024 mmol), cesium carbonate (77 mg, 0.236 mmol), 2-dicyclohexylphosphino-2?-(N,N-dimethylamino)-biphenyl (DavePhos, 18.58 mg, 0.047 mmol), 4-amino-2-fluoropyridine (8.82 mg, 0.079 mmol), and (R)-3-chloro-10-methyl-9,10,11,12-tetrahydro-8H-[1,4]diazepino[5?,6?:4,5]thieno[3,2-f]quinolin-8-one (S1-12) (25 mg, 0.079 mmol) were dissolved in 0.5 mL of dry t-BuOH. The reaction was placed under vacuum then backfilled with nitrogen. The reaction was heated to 100 C. overnight then cooled, filtered and concentrated to dryness. The residue was redissolved in DMSO and purified by reverse phase HPLC with 95%-5% H2O (containing 0.5% TFA v/v)/acetonitrile to afford compound I-3 (0.004 g, 7.8 mumol, 10.0% yield). MS: m/z 393.6 (M+H), 391.7 (M-H). 1H NMR (400 MHz, DMSO-d6): delta 1.13 (d, 3H), 3.39 (m, 2H), 3.55 (m, 1H), 6.94 (br s, 1H), 7.20 (d, 1H), 7.81 (d, 1H), 7.99 (m, 4H), 9.02 (d, 1H), 10.21 (s, 1H).

The synthetic route of 18614-51-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Celgene Avilomics Research, Inc.; Alexander, Matthew David; Chuaqui, Claudio; Malona, John; McDonald, Joseph John; Ni, Yike; Niu, Deqiang; Petter, Russell C.; Singh, Juswinder; (164 pag.)US2016/75720; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 58584-94-4, 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. 58584-94-4, name is 2,6-Dichloro-3-methylpyridine, molecular formula is C6H5Cl2N, 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.

(2d) 2,6-Dichloro-3-methyl-5-nitropyridine [Formula 21]; Anhydrous trifluoromethanesulfonic acid (21.9 ml, 129 mmol) was dropped into a mixture of tetramethyl ammonium nitrate (17.3 g, 127 mmol) and dichloromethane (60 ml) at 0C under nitrogen flow, and the reaction mixture was stirred for 1.5 hours while elevating to room temperature. After a 10: 1.5 mixture (13.7 g) of 2,6-dichloro-3-methylpyridine and 2,4-dichloro-5- methylpyridine in dichloromethane (20 ml) was added and stirred for 30 minutes at room temperature, the reaction mixture was stirred under reflux for 48 hours. The reaction mixture was poured into a saturated sodium bicarbonate solution, and extracted with dichloromethane (200 ml), and after washed with water, dried over magnesium sulfate. The residue obtained by evaporating the solvent was triturated with heptane, thereby yielding the title compound (6.55 g, 31.6 mmol) as a pale brown solid. ¹H NMR (400MHz, DMSO-d6)8 ppm; 2.42(3H, s), 8.70(1H, s).

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 58584-94-4, 2,6-Dichloro-3-methylpyridine.

Reference:
Patent; EISAI CO., LTD.; WO2005/103049; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 20260-53-1, name is Nicotinoyl chloride hydrochloride, molecular formula is C6H5Cl2NO, 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. Formula: C6H5Cl2NO

To a mixture of N-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine, Intermediate 1 (94.8 mg, 0.30 mmol) and isonicotinoyl chloride hydrochloride (56.1 mg, 0.32 mmol) in THF (2.0 mL) at room temperature was added N,N-diisopropylethylamine (0.157 mL, 0.90 mmol). After stirring for 3 hours at room temperature, an additional 21 mg of isonicotinoyl chloride hydrochloride was added and the reaction continued for 17 hours. The reaction was quenched with H2O, then treated with an EtOAc/saturated NaHCO3(aq) solution work-up to give an off-white solid. The solid was recrystallized from EtOAc/hexane to afford a white solid (115 mg, 91%). (0276) 1H NMR (300 MHz, DMSO-d6) delta ppm 2.76-2.95 (m, 2H) 3.52-3.59 (m, 1H) 3.61 (s, 3H) 3.74 (s, 6H) 3.95 (t, J=6.74 Hz, 1H) 4.43 (br. s., 1H) 4.71 (s, 1H) 7.17-7.27 (m, 2H) 7.39-7.56 (m, 2H) 8.19 (s, 0.37H, minor rotamer) 8.42 (s, 0.63H, major rotamer) 8.67-8.74 (m, 2H) 9.44 (br. s., 1H).

With the rapid development of chemical substances, we look forward to future research findings about 20260-53-1.

Reference:
Patent; Allergan, Inc.; Wurster, Julie A.; Malone, Thomas C.; Hull, III, Clarence Eugene; Rao, Sandhya; Yang, Rong; Yee, Richard; (24 pag.)US9296747; (2016); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem