Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 1001413-01-9, 1-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid, 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, SDS of cas: 1001413-01-9, blongs to pyridine-derivatives compound. SDS of cas: 1001413-01-9

Compound 53.3 (0.094 grams, 0.204 mmol) was dissolved in methanol (5 ml). A scoop of palladium on carbon (Degussa Type ElOl NEAV wet) was added followed by 4.0M HCl p-Dioxane (1 ml). This mixture was placed on a Parr shaker at 40 psi for 48 hours, filtered through Celite, and concentrated. This residue was mixed with Compound 20.2 (54 milligrams, 0.204 mmol), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (47 milligrams, 0.245 mmol) and 1-hydroxybenzotriazole monohydrate (38 milligrams, 0.245 mmol), dissolved in N,N-dimethylformamide (2 ml) and diisopropylethylamine (0.178 ml, 1.02 mmol) was added. The reaction was stirred at ambient temperature for 16 hours and then flooded with ethyl acetate, washed with saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered and concentrated to yield Compound 53.4 (2.8 milligrams, 0.006 mmol). ES (+) MS m/e = 461 (M+H). IH NMR (400 MHz, MeOH-d4) delta ppm 4.60 (s, 2 H) 5.14 (s, 2 H) 6.49 (m, 1 H) 6.60 (m, 1 H) 7.11 (m, 2 H) 7.23 (m, 1 H) 7.37 (m, 1 H) 7.83 (m, 1 H) 7.96 (m, 1 H) 8.29 (m, 1 H) 8.40 (m, 1 H) 8.69 (d, J=8.31 Hz, 1 H).

The synthetic route of 1001413-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNESIS PHARMACEUTICALS; BIOGEN IDEC, INC.; WO2008/5457; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 54923-31-8, 5-Bromo-6-methylpyridin-2-ol, 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, 54923-31-8, blongs to pyridine-derivatives compound. Safety of 5-Bromo-6-methylpyridin-2-ol

Step B.4-(5-Bromo-6-methyl-pyridin-2-yloxy)-butyric acid, ethyl ester A mixture of 5-bromo-6-methyl-pyridin-2-ol (1.3 g, 6.9 mmol), 4-bromo-butyric acid ethyl ester (2.7 g, 13.8 mmol) and K2C03 (2.8 g, 20.7 mmol) in DMF (20 mL) was heated at 110C under a dry N2 atmosphere for 16 h. After cooling, the mixture was diluted with 200 mL of H2O, and twice extracted with ethyl acetate. The combined organic phase was washed with brine, dried over anhydrous Na2S04 and concentrated. The residue was purified by flash column chromatography on silica gel (EA/PE=1/10) to give the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54923-31-8, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William K.; LI, Bing; SZEWCZYK, Jason W.; WANG, Bowei; PARKER, Dann; BLIZZARD, Timothy; JOSIEN, Hubert; BIJU, Purakkattle; CHOBANIAN, Harry; GUDE, Candido; NARGUND, Ravi P.; PIO, Barbara; DANG, Qun; LIN, Linus S.; HU, Bin; CUI, Mingxiang; CHEN, Zhengxia; DAI, Meibi; ZHANG, Zaihong; LV, Ying; TIAN, Lili; WO2015/89809; (2015); A1;; ; Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William, K.; LI, Bing; SZEWCZYK, Jason, W.; WANG, Bowei; PARKER, Dann; BLIZZARD, Timothy; JOSIEN, Hubert; BIJU, Purakkattle; CHOBANIAN, Harry; GUDE, Candido; NARGUND, Ravi, P.; PIO, Barbara; DANG, Qun; LIN, Linus, S.; HU, Bin; CUI, Mingxiang; CHEN, Zhengxia; DAI, Meibi; ZHANG, Zaihong; LV, Ying; TIAN, Lili; WO2015/95256; (2015); 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.152460-09-8, name is N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine, molecular formula is C16H13N5O2, molecular weight is 307.31, as common compound, the synthetic route is as follows.Application In Synthesis of N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine

In to a hydrogenation kettle a N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2- pyridineamine (20 g; 0.0.0651 mol) obtained from step-B and methanol (400ml) were added. Wet Raney’s nickel (8g) was washed thoroughly with water and was charged into hydrogenation kettle. Hydrogenation was conducted at 60psi at 25C for 45hours. The reaction mixture was filtered and washed with methanol (200ml). The combined filtrates were concentrated in vacuum, treated with a mixture of water (100ml) and chloroform (200 ml). The organic layer was washed with water (3x50ml) and distilled under vacuum. Residual solid was brought to room temperature and ethyl acetate (150ml) was charged. The solution was heated to reflux temperature and cooled down with stirring to 0-5C. The crystalline solid was filtered off and washed with chilled ethyl acetate (10ml), dried to afford title compound (15.0g, yield: 82.7%) of the title product. Purity (by HPLC): 99.40%) Melting point: 143-147C

At the same time, in my other blogs, there are other synthetic methods of this type of compound,152460-09-8, N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; NATCO PHARMA LIMITED; KOMPELLA, Amala Kishan; RACHAKONDA, Sreenivas; GAMPA, Venu Gopala Krishna; ADIBHATLA, Kali Satya Bhujanga Rao; NANNAPANENI, Venkaiah Chowdary; WO2013/35102; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 108-96-3, Pyridin-4(1H)-one, 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, Product Details of 108-96-3, blongs to pyridine-derivatives compound. Product Details of 108-96-3

Example 45; 4-[[2-(4-Pyridinyloxy)ethyl](2,2,2-trifluoroethyl)amino]-2- (trifluoromethyl)benzonitrile; Synthesized as described in Example 1C from 4-[(2-hydroxyethyl)(2,2,2- trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile and 4-pyridone, using dry DME as reaction solvent: 1H NMR (400 MHz, CDCI3) delta 8.45 (dd, J = 5.0, 1.3 Hz, 2H), 7.68 (d, J = 8.8 Hz, 1 H), 7.18 (d, J = 2.5 Hz, 1 H), 7.01 (dd, J = 8.7, 2.6 Hz, 1 H), 6.77 (dd, J = 4.9, 1.3 Hz, 2H), 4.27 (t, J = 5.2 Hz, 2H), 4.19 (q, J = 8.5 Hz, 2H), 4.04 (t, J = 5.3 Hz, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,108-96-3, Pyridin-4(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/44707; (2006); 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. 69627-02-7, name is Thieno[3,2-b]pyridin-7(4H)-one, molecular formula is C7H5NOS, 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. Safety of Thieno[3,2-b]pyridin-7(4H)-one

A stirred suspension of thieno[3,2-b]pyridin-7-ol (1, 5.0 g, 33.1 mmol) in POCls(15 mL) was heated to 105C in an oil bath for 4 hrs. The resultant solution was cooled toroom temperature and the POCls was removed under reduced pressure. The residue wascooled in an ice/water bath and cold water was added. The water was made basic withconcentrated NlrLtOH solution and extracted with EtOAc. The organic extract was driedover anhydrous sodium sulfate and concentrated to produce an oil which was purified bycolumn chromatography (eluent EtOAc-hexane, 1:4) to afford the title compound as abrown solid (4.5 g, 72% yield). .H NMR (400 MHz, CDC13) 8 (ppm): 8.60 (d, J= 4.9 Hz,1H), 7.80 (d, J= 5.5 Hz, 1H), 7.60 (d, J= 5.5 Hz, 1H), 7.30 (d, J= 4.9 Hz, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 69627-02-7.

Reference:
Patent; METHYLGENE, INC.; WO2006/10264; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 156118-16-0, 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. 156118-16-0, name is 3-Amino-6-bromo-4-methylpyridine. A new synthetic method of this compound is introduced below.

To a solutionof 27(4.00 g, 21.4 mmol) in AcOH (300 ml) was added NaNO2 (1.48 g, 21.4mmol) and stirred overnight at roomtemperature. The reaction mixture was concentrated in vacuo. The residue was diluted with EtOAc and washed with saturatedNaHCO3 aqueous solution and brine. Theorganic layer was dried over anhydrous MgSO4 and reduced underpressure. The residue was purified bysilica gel column chromatography (0-50% EtOAc in hexanes) to afford 28 as a yellow solid (2.48 g, 59%yield).1H NMR (300 MHz, CDCl3): delta ppm7.86 – 7.90 (m, 1 H), 8.09 – 8.14 (m, 1 H), 8.83 – 8.88 (m, 1 H).MS ESI/APCI Dual m/z: 198 [M+H] .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,156118-16-0, its application will become more common.

Reference:
Article; Matsuda, Daisuke; Kobashi, Yohei; Mikami, Ayako; Kawamura, Madoka; Shiozawa, Fumiyasu; Kawabe, Kenichi; Hamada, Makoto; Oda, Koji; Nishimoto, Shinichi; Kimura, Kayo; Miyoshi, Masako; Takayama, Noriko; Kakinuma, Hiroyuki; Ohtake, Norikazu; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3441 – 3446;,
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.94413-70-4, name is 4-(Aminomethyl)-2-methylpyridine, molecular formula is C7H10N2, molecular weight is 122.1677, as common compound, the synthetic route is as follows.Safety of 4-(Aminomethyl)-2-methylpyridine

To a stirred solution of 3-(3,4-dimethoxyphenyl)-8-iodo-2,6-dimethylimidazo[l,2-b]pyridazine (0.1 g, 0.240 mmol) and (2-methylpyridin-4-yl)methanamine (0.06 g, 0.312 mmol) in toluene (2 mL) was added cesium carbonate (0.156 g, 0.48 mmol), 2,2′-bis(diphenylphosphino)-l ,l ‘- binaphthyl (BINAP (7 mg, 0.012 mmol) and Pd(OAc)2 (2 mg, 0.012 mmol). The reaction was stirred at l05C for l6h. Upon completion, the reaction was diluted with 10% MeOH-CH2Cl2 and filtered through a celite bed. The filtrate was concentrated and the obtained solid was washed with acetonitrile to afford 3-(3,4-dimethoxyphenyl)-2,6-dimethyl-N-((2-methylpyridin-4- yl)methyl)imidazo[l,2-b]pyridazin-8-amine (0.09 g, 91.83%) as a pale brown solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,94413-70-4, 4-(Aminomethyl)-2-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; CUROVIR AB; WESTMAN, Jacob; (78 pag.)WO2020/74160; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 5350-93-6, 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.5350-93-6, name is 6-Chloropyridin-3-amine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

A solution of 5-amino-2-chIoropyridine (30.94 g, 236 mmol) and di-tert-butyldicarbonate (65.36 g, 299 mmol) in 1 ,4-dioxane (300 ml.) was stirred at reflux for 20 hours. Additional di- tert-butyldicarbonate (8.30 g, 38 mmol) was added and the reaction was stirred at reflux for 7 hours. The reaction was cooled to room temperature and poured into water. The Jayers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and solvent was removed at reduced pressure to give a brown oil. The oil was triturated with diethyl ether and filtered to give tert-butyl 6-chloropyridin-3-ylcarbamate as a tan solid. (49.84 g, 92% yield). 1H NMR (CDCI3) delta 8.24 (m, 1 H)1 7.96 (m, 1 H), 7.27 (m, 1 H), 6.65 (br s, 1 H), 1.51 (s, 9H).

The chemical industry reduces the impact on the environment during synthesis 5350-93-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY LLC; WO2006/126083; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1480-64-4, 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 1480-64-4, name is 3-Chloro-2-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

3-Chloro-2-fluoropyridine (5.00 g, 37.25 mmol, 1 eq.) and benzylamine (5.75 mL, 52.15 mmol, 1.4 eq.) were addedto cesium carbonate (18.21 g, 55.88 mmol, 1.5 eq.) in dimethyl sulfoxide (25 mL) and the reaction mixture wasstirred at 105 C for 7 h. After cooling to 25 C water (25 mL) was added dropwise using an ice bath to maintain thetemperature below 30C. The reaction mixture was transferred to a separation funnel. Then water (15 mL) andethyl acetate (40 mL) were added and the phases were separated. The aqueous phase was extracted with ethylacetate (2 x 50 mL). The combined organic phases were washed with water (4 x 50 mL) and brine (50 mL). Dryingover magnesium sulfate, removal of the solvent and purification by flash chromatography (2 to 3% ethyl acetate inheptanes) gave the N-benzyl-3-chloropyridin-2-amine as a white solid (6.56 g, 81%). Rf = 0.25 (5% ethyl acetate inheptanes).1H NMR (400 MHz, CDCl3): = 1H NMR (400 MHz, CDCl3): = 4.71 (d, J = 5.5 Hz, 2 H), 5.28 (br. s, 1 H), 6.57 (dd, J =7.8, 5.0 Hz, 1 H), 7.27 – 7.32 (m, 1 H), 7.33 – 7.42 (m, 4 H), 7.46 -7.51 (obs. m, 1 H), 8.07 (dd, J = 4.9, 1.6 Hz, 1 H).13C NMR (101 MHz, CDCl3): = 45.5, 113.1, 115.4, 127.3, 127.7, 128.6, 136.1, 139.3, 146.0, 153.9.LC/MS (m/z): [M + H]+ calculated for C12H12ClN2+, 219.1 ; found, 218.7

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 1480-64-4, 3-Chloro-2-fluoropyridine.

Reference:
Article; De Gasparo, Raoul; Lustenberger, Philipp; Mathes, Christian; Schlama, Thierry; Veitch, Gemma E.; Le Paih, Jacques J. M.; Synlett; vol. 26; 2; (2015); p. 197 – 200;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 5470-17-7 , The common heterocyclic compound, 5470-17-7, name is 3-Bromo-2-chloro-5-nitropyridine, molecular formula is C5H2BrClN2O2, 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 1: 2-(3-bromo-5-nitropyridin-2-yloxy)-N, N-dimethylethanamine (Intermediatell).To a stirred solution of S-bromo-l-chloro-S-nitropyridine (2.5 g, 10.53 mmol) and 2-(dimethylamino) ethanol (1.877 g, 21.06 mmol) in DMF (10 mL) was added portion wise potassium carbonate (2.91 g, 21.06 mmol) and the mixture was stirred at 60 0C for 2- 3 hrs. Reaction mixture was cooled to RT, diluted with ethyl acetate (50-7OmI), washed with water and then brine, organic layer was collected, dried over sodium sulfate and concentrated in vacuo to give crude 2-(3-bromo-5-nitropyridin-2-yloxy)-N, N- dimethylethanamine (2.70 g, 88 %) as brown liquid. The crude material was taken for next step without further purification. MS (ES+): 292 for C9H12BrN3O3

The synthetic route of 5470-17-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/147431; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem