Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 63897-12-1, 2,4-Dichloro-6-methyl-3-nitropyridine, 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, 63897-12-1, blongs to pyridine-derivatives compound. Safety of 2,4-Dichloro-6-methyl-3-nitropyridine

EXAMPLE 1022-[2-(1 ,3-benzothiazol-5-yl)-1 H-imidazol-4-yl]-6-methyl-1 -[2-(methyloxy)ethyl]-4-(4- mor holinyl)-1 H-imidazo[4,5-c]pyridineStep 1 . 2-chloro-6-methyl-N-[2-(methyloxy)ethyl]-3-nitro-4-pyridinamineTo a solution of 2,4-dichloro-6-methyl-3-nitropyridine (1 g, 4.83 mmol) and triethylamine (0.741 ml, 5.31 mmol) in Nu,Nu-Dimethylformamide (DMF) (1.959 ml) at 0 C was added a solution of 2-methoxyethlyamine (0.424 ml, 4.88 mmol) in Nu,Nu-Dimethylformamide (DMF) (0.535 ml). Removed from ice bath and stirred at rt overnight. LCMS showed mainly desired product along with a small amount of the undesired regioisomer as well as the bis addition product. Quenched with water and diluted with Et20. Separated and extracted twice more with Et20. Washed combined organics with water twice, then with brine, dried on MgS04, filtered and concentrated. Purified via Biotage FCC (0-20% EtOAc / hex) Desired and bis-addition product co-eluted. Combined all product-containing fractions and concentrated resulting in a bright yellow solid. Suspended in hexanes, sonicating to break up large particles. Sonicated for 20 min. Filtered and collected bright yellow solid that was pure desired product: 2-chloro-6-methyl-N-[2-(methyloxy)ethyl]-3-nitro-4- pyridinamine (466 mg, 1.897 mmol, 39.3 % yield). MS (m/z): 246.1 (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,63897-12-1, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; BODMER, Vera, Q.; CASILLAS, Linda, N.; DEMARTINO, Michael, P.; KING, Bryan, W.; LAKDAWALA SHAH, Ami; LEISTER, Lara, Kathryn; WANG, Gren, Z.; WISNOSKI, David, Duff; HARRIS, Philip, A.; RAMANJULU, Joshi, M.; ROMANO, Joseph, J.; WILSON, Matthew, A.; WO2011/123609; (2011); A1;,
Pyridine – Wikipedia,
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Reference of 98198-48-2, 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 98198-48-2 as follows.

A mixture of 2-amino-5-bromo-4-methylpyridine (2.0 g, 10.7 mmol) and CuCN (1.1 g, 12.3 mmol) in DMF (2.5 mL) wasrefluxed for 4 h. After the mixture was cooled to room temperature, NaCN (2.15 g) and H2O (6.5mL) were added, and the mixture was stirred and extracted by AcOEt. The solution was washedby aq. 10% CuCN and brine. After the solvent was removed under vacuo, the residue waschromatographed on silica gel (AcOEt/hexane = 1 : 1) to give 2-amino-5-cyano-4-methylpyridine (829 mg, 58%). A solution of 2-amino-5-cyano-4-methylpyridine (706 mg, 5.3mmol) in EtOH (8.8 mL) and aq. 10N NaOH (8.8 mL) was refluxed for 24 h. After cooled toroom temperature, the mixture was diluted by adding H2O (35 mL), neutralized by aq. HCl, and filtered. The solid was washed by ether and H2O to give 6-amino-4-methylpicolinic acidcontaining NaCl (879 mg), which was dissolved in MeOH (16 mL). To this mixture was addedSOCl2 (0.7 mL, 6.7 mmol) and the mixture was refluxed for 20 h. After cooled to roomtemperature, the solvent was removed under vacuo. To the residue H2O (20 mL) was added andpH was adjusted to 13 by aq. 1N NaOH and filtered. The solid was washed by H2O and driedunder vacuo to give 2-amino-5-methoxycarbonyl-4-methylpyridine (484 mg), which wasdissolved in aq 15% H2SO4 (10.4 mL). To the solution was added NaNO2 (402 mg, 5.81 mmol)at 0 C and the mixture was stirred for 2 h at 0 C and, then, 2 h at room temperature. Themixture was extracted by AcOEt and the solvent was removed under vacuo. The residue waschromatographed on silica gel (AcOEt) to give 2bd (105 mg, 21%):

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,98198-48-2, its application will become more common.

Reference:
Article; Yamaguchi, Ryohei; Kobayashi, Daiki; Shimizu, Mineyuki; Fujita, Ken-ichi; Journal of Organometallic Chemistry; vol. 843; (2017); p. 14 – 19;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 824429-51-8, Adding some certain compound to certain chemical reactions, such as: 824429-51-8, name is tert-Butyl (2-(hydroxymethyl)pyridin-3-yl)carbamate,molecular formula is C11H16N2O3, 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 824429-51-8.

N- [2- (hydroxymethyl) pyridin-3-yl] carbamic acid tert-butyl ester(0.15 g) in dichloromethane (1 mL)Thionyl chloride (0.096 g) was added, and the mixture was stirred at room temperature for 1 hour.The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and the crude product was extracted with dichloromethane. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane)To give N- [2- (chloromethyl) pyridin-3-yl] carbamic acid tert-butyl ester (0.12 g).A mixture of the product (0.12 g), dichloromethane (2 mL), potassium cyanide (0.039 g), tetrabutylammonium hydrogen sulfate (0.017 g) and water (0.5 mL) was stirred at room temperature for 3 hours. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the crude product was extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane)To give N- [2- (cyanomethyl) pyridin-3-yl] carbamic acid tert-butyl ester.Concentrated hydrochloric acid (0.072 g) and 10% palladium on carbon (50% wet, 0.03 g) were added to the product methanol (3 mL) – dichloromethane (3 mL) mixture, and the mixture was stirred at room temperature under a hydrogen atmosphere (0.32 MPa) Followed by stirring. The reaction mixture was passed through a celite pad and the filtrate was concentrated under reduced pressure. The residue was purified by aminopropyl silica gel column chromatography (eluent: ethyl acetate / methanol) to give the title compound (0.011 g). Structural formula, spectral data and purification conditions are shown in Table 26.

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. 824429-51-8, tert-Butyl (2-(hydroxymethyl)pyridin-3-yl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; Hirasawa, Hideaki; Tanada, Fumiya; Mutai, Yousuke; Fushimi, Nobuhiko; Kobayashi, Junichi; Kijima, Yoshiro; (267 pag.)JP2018/108988; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 775288-71-6, 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. 775288-71-6, name is 1-(6-Nitropyridin-3-yl)piperazine, molecular formula is C9H12N4O2, 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.

A mixture of 5-Bromo-2-nitropyridine (203 g, 1.37 mol), piperazine (153 g, 1.77 mol), tetrabutylammonium iodide (25.2 g, 0.068 mol), and potassium carbonate (207 g, 1.50 mol) in dimethyl sulfoxide (2.6 L) was stirred at 80C overnight. The resultant reaction mixture was cooled to room temperature, and the mixture was poured into water (7 L). The resultant solid was collected by filtration, and the solid was washed with dichloromethane (1 L × 2) and dried. The filtrate was extracted with chloroform (2 L × 7). The resultant organic phase was washed with water (2 L) and then with saturated brine (2 L), and the organic phase was concentrated under reduced pressure to yield solid. The resultant solid products were combined together and used for the subsequent reaction without further purification. (0173) The solid product (490 g) was dissolved in THF (2 L) and water (500 mL), and sodium hydrogen carbonate (119 g, 1.42 mol) was added to the solution. To the resultant suspension was added di-tert-butyl dicarboxylate (262 g, 1.2 mol), and the mixture was stirred at room temperature for three hours. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with water (1 L) and extracted with dichloromethane (1 L × 3). The resultant organic phases were combined together and then washed with water (1 L). The aqueous phase was extracted with dichloromethane (300 mL). The resultant organic phases were combined together and dried over anhydrous magnesium sulfate. The solid was separated by filtration, and the filtrate was concentrated under reduced pressure. The resultant solid was suspended in ethyl acetate (2 L) and heated to 60C, and the solid was separated by filtration at 60C. The solid was dried under reduced pressure to yield the title compound (191 g, 62%) APCI-MS (M+H)+ 309.1, C14H20N4O4=308.15 1H-NMR delta(400 MHz, CDCl3) : 8.16 (d, J=9 Hz, 1H), 8.11 (d, J=3 Hz, 1H), 7.19 (dd, J=9.3 Hz, 1H), 3.64-3.61 (m, 4H), 3.45-3.42 (m, 4H), 1.47 (s, 9H)

According to the analysis of related databases, 775288-71-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Teijin Pharma Limited; MIZUNO, Tsuyoshi; SHIMADA, Tomohiro; UNOKI, Gen; EBISAWA, Masaru; TAKEUCHI, Susumu; MINAMIZONO, Kunio; SASAKI, Kosuke; YOKOSAKA, Takuya; IGARASHI, Junji; MARUYAMA, Akinobu; TAKAHASHI, Hiroshi; HORIE, Kyohei; SAKAI, Yuri; (447 pag.)EP3305785; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1228014-35-4, Adding some certain compound to certain chemical reactions, such as: 1228014-35-4, name is tert-Butyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate,molecular formula is C12H13BrN2O2, 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 1228014-35-4.

j0704j A solution of tert-butyl 4-bromo-1H-pyrrolo[2,3-bjpyridine-1-carboxylate (XCII) (2 g, 6.8 mmol, 1.0 eq), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)-1,3,2-dioxaborolane (2.07 g, 8.16 mmol, 1.02 eq), KOAc (1.99 g, 20.4 mmol, 3 eq) in dioxane (25 mL) was degassed (x 3) with a water pump. Pd(dppf)C12 (246 mg, 0.34 mmol, 0.05 eq) was then added quickly in one portion under nitrogen. The reaction was stirred at 90C for 6 h. Water (100 mL) was added and extracted with EtOAc (x 3). Flash chromatography (PE: EtOAc 20:1) gave tert-butyl 4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1H-pyrrolo[2,3 -bjpyridine- 1- carboxylate (C) as a green oil (2.0 g, 5.82 mmol, 86.4%). ?H NMR (CDC13, 400 MHz) ppm 1.39 (s, 12H), 1.67 (s, 9H), 6.93 (d, J4Hz, 1H), 7.54 (d, J4.8Hz, 1H), 7.65 (d, J4Hz, 1H), 8.51 (d, J4.4Hz, 1H); ESIMS found for C,8H25BN204 mlz 345.1 (M+H).

According to the analysis of related databases, 1228014-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (274 pag.)WO2017/24021; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 131748-14-6, Adding some certain compound to certain chemical reactions, such as: 131748-14-6, name is 4-Chloro-(2-trifluoromethyl)pyridine,molecular formula is C6H3ClF3N, 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 131748-14-6.

NaH (60% dispersion in mineral oil, 46 mg, .1.19 mmol) was added portionwise to a stirred solution of l-Boc-4-hydroxypiperidine (CAS: 109384-19-2; 200 mg, 0.99 mmol) in DMF (3 mL) in a sealed tube and under N2 at 0 C. The reaction mixture was stirred at 0 C for 30 min and a solution of 4-chloro-2-(trifluoromethyl)pyridine (CAS: 131748- 14-6; 271 mg, 1.49 mmol) in DMF (2 mL) was added dropwise at 0 C. The reaction mixture was stirred at 60 C for 48 h. The mixture was concentrated in vacuo. The residue was diluted with water and extracted with EtOAc. The organic layer was dried (Na2S04), filtered and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica, EtOAc in DCM, gradient from 0:100 to 50:50). The desired fractions were collected and concentrated in vacuo to afford intermediate 104 (212 mg, 62%) as colorless oil which solidified to a white solid upon standing

According to the analysis of related databases, 131748-14-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; DE LUCAS OLIVARES, Ana Isabel; DELGADO-JIMENEZ, Francisca; CONDE-CEIDE, Susana; VEGA RAMIRO, Juan, Antonio; (245 pag.)WO2019/243530; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89284-61-7, 4-Chloronicotinonitrile, 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, 89284-61-7, blongs to pyridine-derivatives compound. Safety of 4-Chloronicotinonitrile

Step B: Preparation of 4-((lr,4r)-4-(l-(5-(2-Fluoropropan-2-yl)-l,2,4-oxadiazol-3- yl)piperidin-4-yloxy)cyclohexyloxy)nicotinonitrile (Compound 10).Potassium 2-methylpropan-2-olate (0.293 mL, 0.293 mmol) was added to a solution of( 1 r,4r)-4-( 1 -(5-(2-fluoropropan-2-yl)- 1 ,2,4-oxadiazol-3-yl)piperidin-4-yloxy)cyclohexanol (0.08 g, 0.24 mmol) and 4-chloronicotinonitrile (40.6 mg, 0.293 mmol) in THF (2.4 mL) at room temperature. The reaction mixture was stirred at room temperature for 1.5 h and then was diluted with DCM and washed with saturated aqueous NaHC03. The DCM layer was dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography (silica gel, 0-5% MeOH in DCM) and then HPLC to give the title compound (47 mg). LCMS m/z = 430.4 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.57-1.70 (m, 4H), 1.75-1.84 (m, 8H), 1.87-1.94 (m, 2H), 1.96-2.05 (m, 2H), 2.12-2.21 (m, 2H), 3.22-3.29 (m, 2H), 3.60-3.70 (m, 2H), 3.75-3.81 (m, 2H), 4.73-4.79 (m, 1H), 7.13 (d, J = 4.5 Hz, 1H), 8.71-8.84 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89284-61-7, its application will become more common.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert, M.; BUZARD, Daniel, J.; HAN, Sangdon; KIM, Sun, Hee; LEHMANN, Juerg; WO2012/170702; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 59718-84-2, 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 59718-84-2, name is Methyl 3-methylpicolinate. This compound has unique chemical properties. The synthetic route is as follows.

A solution of methyl 3-methylpyridine-2-carboxylate (800 mg, 5.29 mmol, 1.00 equiv) and 3-chloroperoxybenzoic acid (1826 mg, 10.58 mmol, 2.00 equiv) in dichloromethane (20 mL) was stirred for 4 hours at 45 C. The resulting solution was concentrated under vacuum and the residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1:3). This resulted in the title compound (850 mg, 96%) as yellow oil. LC-MS (ES, mlz): 168 [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 59718-84-2, Methyl 3-methylpicolinate.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; LIN, Xingyu; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25026; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16133-25-8, Pyridine-3-sulfonyl chloride, 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, 16133-25-8, blongs to pyridine-derivatives compound. Recommanded Product: 16133-25-8

Reference Example 23; tert-butyl { [5-bromo-l- (pyridin-3-ylsulfonyl) -lH-pyrrol-3- yl]methyl }methylcarbamate; To a suspension of sodium hydride (60percent in oil, 7.4 g) in tetrahydrofuran (300 mL) was added a solution of tert-butyl [ (5-bromo-lH-pyrrol-3-yl) methyl]methylcarbamate (44.5 g) in tetrahydrofuran (60 mL) at 0°C, and 15-crown-5 (40.7 g) and pyridine-3-sulfonyl chloride (30.1 g) were added at the same temperature. The mixture was stirred at room temperature for 30 min, water was added and the mixture was concentrated under reduced pressure. The residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was washed with a mixed solvent of diisopropyl ether-hexane=l : 1 to give the title compound as colorless crystals (yield 45.2 g, 68percent) . 1H-NMR (CDCl3) delta: 1.47(9H,s), 2.80 (3H,brs) , 4.18 (2H,brs) ,6.28(lH,brs) , 7.35 (lH,brs) , 7.48-7.52 (IH,m) , 8.18-8.22 (lH,m) , 8.85-8.88 ( IH,m), 9.12-9.13 (IH, m) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16133-25-8, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/108380; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 34552-13-1, 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.34552-13-1, name is 2-Chloro-5-methylpyridin-3-amine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.

Step A: 2,6-Dichloro-5-methylpyridin-3-amine. NCS (32.9 g, 246 mmol) was added in portions to a solution of 2-chloro-5-methylpyridin-3-amine (35.0 g, 245 mmol) and acetonitrile (250 mL). The resulting mixture was heated at 35 C. for 16 hours before cooling to room temperature. The resulting suspension was filtered, and the filtrate concentrated to dryness under reduced pressure. The residue was purified by flash chromatography (eluent:petroleum ether/ethyl acetate; 1:0 to 4:1, gradient elution) to afford the title compound (45 g, 99%). MS (ESI): mass calcd. For C6H6Cl2N2 176.0 m/z found 176.8 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta 7.07 (s, 1H), 5.65 (br s, 2H), 2.53 (s, 3H).

Statistics shows that 34552-13-1 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-methylpyridin-3-amine.

Reference:
Patent; Janssen Pharmaceutica NV; Barbay, J. Kent; Chai, Wenying; Hirst, Gavin C.; Kreutter, Kevin D.; Kummer, David A.; McClure, Kelly J.; Nishimura, Rachel T.; Shih, Amy Y.; Venable, Jennifer D.; Venkatesan, Hariharan; Wei, Jianmei; (501 pag.)US2020/55874; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem