Day: September 29, 2021

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.867267-24-1, name is 2,5-Dimethoxypyridine, molecular formula is C7H9NO2, molecular weight is 139.1519, as common compound, the synthetic route is as follows.Recommanded Product: 867267-24-1

General procedure: At -78 C., lithium diisopropylamide (2 M in tetrahydrothranlheptane/ethylbenzene) was added to a solution of the appropriate pyridine derivative in tetrahydrofuran (3 ml/mmol), the mixture was stirred for 2-4 h and triisopropyl borate was then added quickly. The reaction mixture was maintained at -78 C. for a further 2-3 hand then slowly thawed to RT overnight. Afier addition of water, the tetrahydrofuran was removed under reduced pressure and the aqueous phase was extracted twice with ethyl acetate. The aqueous phase was acidified with aqueous hydrochloric acid (2M), generally resulting in formation of a precipitate which was filtered off, washed with water and dried. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried (sodium sulphate or magnesium sulphate), filtered and concentrated under reduced pressure.;11.53 g (82.9 mmol) of 2,5-dimethoxypyridine were reacted according to General Method l. The desired product precipitated out after acidification of the aqueous phase. Yield: 9.53 g (61% of theory)10599] LC/MS [Method 1]: R=0.47 mm; MS (ESIpos):mlz=184 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,867267-24-1, 2,5-Dimethoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; ROeHRIG, Susanne; HILLISCH, Alexander; STRASSBURGER, Julia; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; BUCHMUeLLER, Anja; GERDES, Christoph; SCHAeFER, Martina; TELLER, Henrik; JIMENEZ NUNEZ, Eloisa; SCHIROK, Hartmut; KLAR, Juergen; (66 pag.)US2016/272637; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 916325-85-4 , The common heterocyclic compound, 916325-85-4, name is 5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid, molecular formula is C7H4BrN3O2, 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.

Compound Ic (1.0 g, 4.13 mrnol) and 3-(t°7?-butyl-dimethyl-si]anyloxymethyl)- benzene-l,2-diamine Compound 6a (1.05 g, 4.17 mmol), HATU (1.58 g, 4.16 mmol) EPO and DIPEA (2.5 mL, 35.9 mmol) in DMF (50 mL) was stirred at room temperature overnight. The solvent was removed and the residue was dissolved in ethyl acetate (100 mL), then sequentially washed with hydrochloric acid (20 mL, IM), water (30 mL x 3) and brine (20 mL). The organic solution was evaporated to dryness, in vacuo and purified by silica gel chromatography (10% to 50% of ethyl acetate in hexanes) to yield 5-bromo-lH-pyrazolo[3,4-b]pyridine-3-carboxylic acid [2-amino-3-(tert-butyl- dimethyl-silanyloxymethyl)-phenyl]-amide Compound 6b (1.21g, 61% yield) as a yellow powder. 1H NMR (300 MHz, CDCl3) delta 8.91 (d, IH, J = 2.1 Hz), 8.73 (s, IH), 8.67 (d, IH, 7 = 2.1 Hz), 7.47 (d, IH, 7 = 7.2 Hz), 7.01 (d, IH, 7 = 7.2 Hz), 6.83 (t, IH, J = 7.2 Hz), 4.78 (s, 2H), 0.95 (s, 9H), 0.11 (s, 6H); MS (ESI) m/z: 477 (M+H+).

The synthetic route of 916325-85-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2006/130673; (2006); 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. 10177-31-8, name is 4-Methoxynicotinic acid. A new synthetic method of this compound is introduced below., name: 4-Methoxynicotinic acid

[0350] A solution of 4-(4-(2,4-difluorophenoxy)piperidin-l -yl)-6-methoxypyridin-3-amine (40 mg, 0.1 19 mmol), 4-methoxynicoiinic acid (36.5 mg, 0.239 mmol), HATU (91 mg, 0.239 mmol) and DIPEA (0,052 mL, 0,298 mmol) m NMP (0.5 mL) was heated at 50C for 8 hours. More HATU (50 rng) was added and the reaction mixture was heated at 50C for 17 hours. The solution was diluted with DMF (0.3 mL) and MeOH (0.2 mL) and purified by preparative HPLC, eluting with ACN/water (basic mode) to give the title compound as a white solid (34 mg, 61 %). NuMKappa (500 MHzeta, DMSO-ifc) delta ppm 1.74 – 1.84 (m, 2 H), 2.04 (ddd, J=9.52, 6.35, 3, 17 Hz, 2 H), 2.90 (ddd,./ 12.08. 8.91, 2.93 Hz, 2 H), 3.19 – 3.27 (rn, 2 H), 3.83 (s, 3 H), 4.07 (s, 3 H), 4.51 (tt, J-8.05, 3.91Hz, 1H), 6.48 (s, 1H), 6.97 – 7.05 (m, 1H), 7.25 – 7.34 (m, 3 H), 8.56 (s, 1 1 1). 8.61 (d,.7=5.86 Hz, 1H), 8,90 (s, 1H), 9.65 (s, 1H); ESI-MS m/z [M+H]+ 471.

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, 10177-31-8, 4-Methoxynicotinic acid.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 40381-90-6, 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 40381-90-6, name is 2,6-Dichloropyridine-3-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 2,6-dichioronicotinonitrile (050 g, 2.89 mmoi) in MeOH (10 mL)was added sodium methanolate (0.62 g, 2.89 mmol) at ambient temperature. The reactionmixture was stirred at 60 C for 12 h. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure, diluted with water (40 ml) 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. The residue was purified by preparativeHPLC [Xbridge Phenyl (21.2 x 250 ID) 5 micron; Solvent A: 0.1% TFA, Solvent B:Acetonitrile, Gradient: 5-25% B over 25 mm, Flow: 20 mL/minj to 23A (0.48 g, 19%) as an off white solid. ?HNMR (400 MHz, CDCI3) ppm 4.08 (s, 3 H). 7.01 — 7.03 (d, J= 7.2 Hz, I H), 7.80 7.82 (s, J= 8.0 Hz, IH). LCMS MethodD): retention time 1.94 mm, [M+H] 169.2.

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 40381-90-6, 2,6-Dichloropyridine-3-carbonitrile.

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

Synthetic Route of 19337-97-4, 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.19337-97-4, name is trans-3-(3-Pyridyl)acrylic acid, molecular formula is C8H7NO2, molecular weight is 149.15, as common compound, the synthetic route is as follows.

General procedure: Compound 1c-9c (1.0mmol) was dissolved in anhydrous tetrahydrofuran (20mL). To the solution, triethylamine (1.2mmol) was slowly added and the solution was cooled to-20C, pivaloyl chloride (1.2mmol) was then added, and the reaction mixture was stirred for about 45min. Next, the compound 13 or 15 and n-butyllithium were added to the reaction solution and stirred for 1h, checked for product formation via TLC. Then saturated aqueous solution of ammonium chloride (10mL) was added to quench the n-butyllithium in the reaction and extracted with ethyl acetate, the organic phase was washed with saturated brine (30mL×3), Dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (PE/EA=3: 1) to afford 1-9.

Statistics shows that 19337-97-4 is playing an increasingly important role. we look forward to future research findings about trans-3-(3-Pyridyl)acrylic acid.

Reference:
Article; Zou, Yu; Yan, Chang; Zhang, Huibin; Xu, Jinyi; Zhang, Dayong; Huang, Zhangjian; Zhang, Yihua; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 313 – 319;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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