Tag: M.W:200-300

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 942947-95-7, 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 942947-95-7 as follows.

To a mixture of 5-bromo-4-chloro-3-nitro-pyridin-2-ylamine (0.126 g, 0.50 mmol) and isopropanol (9 ml) was added 2-(piperazin-1-yl)-1-(pyrrolidin-1-yl)ethanone (0.108 g, 0.55 mmol) followed by diisopropylethylamine (0.10 ml, 0.55 mmol). The reaction mixture was heated at 45 C. for 22 h, then allowed to cool to room temperature and the solvents were removed in vacuo. The residue was absorbed on silica gel and the free running powder was placed on a 10 g isolute silica column which was eluted with 70% ethyl acetate in dichloromethane and then 90% ethyl acetate in dichloromethane. The title compound was obtained as a yellow solid (0.162 g, 78%); 1H-NMR (500 MHz, DMSO-d6) 1.74 (m, 2H) and 1.85 (m, 2H) (pyrrolidine 3-CH2 and 4-CH2), 2.60 (br s, 4H, piperazine N(CH2)2), 3.04 (br s, 4H, piperazine N(CH2)2), 3.16 (s, 2H, NCH2CO), 3.27 (t, J=6.90 Hz, 2H) and 3.45 (t, J=6.70 Hz, 2H) (pyrrolidine 2-CH2 and 5-CH2), 7.02 (s, 2H, NH2), 8.16 (s, 1H, 6-H);LC (Method B)-MS (ESI, m/z) Rt=1.89 min-413, 415 [(M+H)+, Br isotopic pattern].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,942947-95-7, its application will become more common.

Reference:
Patent; THE INSTITUTE OF CANCER RESEARCH; US2009/247507; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 72587-15-6, 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 72587-15-6 as follows.

A microwave reaction vial was charged with 2-chloro-3-nitro-5- (trifluoromethyl)pyridine (2 g, 8.83 mmol), NMP (4.41 ml) and CuCN (0.830 g, 9.27 mmol). The vial was sealed and the mixture was irradiated in the MW at 175 C for 15 min. Upon cooling to RT, the reaction mixture was poured onto ice and EtOAc was added. The mixture was filtered through Celite, washing with EtOAc and a small amount of MeOH. The layers of the filtrate were separated, and the aqueous portion was extracted again with EtOAc. The combined organic portions were dried with sodium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography, using a gradient of 0-30% EtOAc in heptane to provide 3-nitro-5- (trifluoromethyl)picolinonitrile (645 mg, 2.97 mmol, 33.7 % yield) as a yellow oil that solidified upon standing. LC/MS (ESI) m/z = 218.1 (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,72587-15-6, its application will become more common.

Reference:
Patent; AMGEN INC.; MINATTI, Ana Elena; LOW, Jonathan, D.; ALLEN, Jennifer, R.; AMEGADZIE, Albert; BROWN, James; FROHN, Michael, J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul, E.; LOPEZ, Patricia; MA, Vu Van; NISHIMURA, Nobuko; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert, M.; SHAM, Kelvin; SMITH, Adrian, L.; WHITE, Ryan; XUE, Qiufen; WO2014/138484; (2014); 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. 119285-07-3, name is tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H22N4O2, 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. category: pyridine-derivatives

A mixture of 3-chloro-5-[(3R)-3-(3-methyl-2-oxoimidazolidin-l-yl)piperidin-l- yl]pyrazine-2-carbonitrile (322 mg, 1.00 mmol), tert- butyl 4-(5-aminopyridin-2- yl)piperazine-l -carboxylate (293 mg, 1.05 mmol), (acetyloxy)palladio acetate (74 mg, 0.33 mmol), [2′-(diphenylphosphanyl)-[l, T-binaphthalen]-2-yl]diphenylphosphane (206.27 mg, 0.33 mmol) and CS2CO3 (981 mg, 3.01 mmol) was degassed and backfilled with N2 5 times. The mixture was allowed to stir at 100 C for 90 min. The mixture was filtered through Celite washing with MeOH/EtOAc, concentrated and purified by MPLC (0-100% EtOAc in CH2CI2) to afford /er/-butyl 4-[5-({3-cyano-6-[(3R)-3-(3-methyl-2-oxoimidazolidin-l- yl)piperidin- 1 -yl]pyrazin-2-yl } amino)pyridin-2-yl]piperazine- 1 -carboxylate (0.2920 g, 51.7%).

With the rapid development of chemical substances, we look forward to future research findings about 119285-07-3.

Reference:
Patent; NURIX THERAPEUTICS, INC.; ROBBINS, Daniel, W.; SANDS, Arthur, T.; MCINTOSH, Joel; MIHALIC, Jeffrey; WU, Jeffrey; KATO, Daisuke; WEISS, Dahlia; PENG, Ge; (415 pag.)WO2020/81450; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 88511-27-7, Adding some certain compound to certain chemical reactions, such as: 88511-27-7, name is 4-Amino-3-iodopyridine,molecular formula is C5H5IN2, 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 88511-27-7.

General procedure: a suspension of 3-iodo-4-aminopyridine (1 mmol), methyl 2-mercaptoacetate (1.5 equiv), copper (I) iodide (0.05 mmol), trans-N,N’-dimethylcyclohexane-1,2-diamine (0.1 mmol) and cesium carbonate(2 equiv) in dry 1,4-dioxane (4 mL) in a vial was degassed by bubbling N2 into the suspension for 3 min while stirring. The vial was then capped tightly. The mixture was heated at 100 C (oil bath temperature) for 15 h. After coolingto rt, filtration was carried out. The combined filtrates were concentrated on rotavap and the residue was subjected to silica gel column chromatographpurification (5% methanol in methylene chloride) furnishing 3b as a beige solid. 1H NMR (400 MHz, CD3OD) d 8.42 (s, 1H, ArH), 8.26 (s, 1H, ArH), 6.96 (d,J = 5.4 Hz, 1H, ArH), 3.40 (s, 2H, CH2). 13C NMR (400 MHz, CD3OD) d 167.4,148.4, 148.1, 146.0, 29.6.

According to the analysis of related databases, 88511-27-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Huang, Wei-Sheng; Xu, Rongsong; Dodd, Rory; Shakespeare, William C.; Tetrahedron Letters; vol. 54; 38; (2013); p. 5214 – 5216;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1211534-25-6, 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.1211534-25-6, name is 4-Bromo-5-chloro-2-methoxypyridine, molecular formula is C6H5BrClNO, molecular weight is 222.47, as common compound, the synthetic route is as follows.

[00266j 28F. 4-(4-(Qert-Butyldimethylsilyl)oxy)-3 -fluoropiperidin- 1 -yl)-5 -chloro-2- methoxypyridine: A mixture of 28E (194 mg, 0.830 mmol), 27B (185 mg, 0.830 mmol) and SPhos precatalyst (6.0 mg, 8.3 jimol) in THF (1.7 mL) was purged with argon and a 1 M solution of LHMDS in THF (1.0 mL, 1.0 mmol) was added. The reaction mixturewas heated to 70 C for 2 h and then cooled to rt. Sat. aq. NaHCO3 (10 mL) was added slowly to the reaction mixture. The mixture was then extracted with EtOAc (2 x 10 mL) and the combined organic extracts were washed with water (20 mL) and brine (20 mL), dried (Na2504), filtered, and concentrated. Purification by silica chromatography gave 28F (182 mg, 0.490 mmol, 58% yield). LC-MS Anal. Calc?d for C17H28C1FN2O2Si:374.16,found[M+H] 374.9.

The chemical industry reduces the impact on the environment during synthesis 1211534-25-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ELLSWORTH, Bruce, A.; JURICA, Elizabeth, A.; SHI, Jun; EWING, William, R.; YE, Xiang-Yang; WU, Ximao; ZHU, Yeheng; SUN, Chongqing; WO2014/78609; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 95652-77-0, 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.95652-77-0, name is Methyl 2-chloro-6-methoxynicotinate, molecular formula is C8H8ClNO3, molecular weight is 201.61, as common compound, the synthetic route is as follows.

To a reaction vial containing 7-amino-4-chloro-isoindolin-l-one (365 mg, 2.0 mmol) in dioxane (2.0 mL) was added methyl 2-chloro-6-methoxynicotinate (603 mg, 3.0 mmol), cesium carbonate (1.3 g, 4.0 mmol), copper iodide (152 mg, 80 mmol) and (S,2S)- Nl,N2-dimethylcyclohexane-l,2-diamine (227 mg, 1.6 mmol). The mixture was purged with nitrogen, then warmed to 110 C. The reaction was stirred at 110 C and monitored by LC- MS. Following completion, the reaction was allowed to cool and was then filtered through Celite and rinsed with ethyl acetate. The crude was purified by silica gel chromatography (0- 50% ethyl acetate/hexane) to give the product.

Statistics shows that 95652-77-0 is playing an increasingly important role. we look forward to future research findings about Methyl 2-chloro-6-methoxynicotinate.

Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean, R.; FAN, Junfa; KALISIAK, Jaroslaw; KRASINSKI, Antoni; LELETI, Manmohan, Reddy; MALI, Venkat; MCMAHON, Jeffrey; SINGH, Rajinder; TANAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; (198 pag.)WO2017/87607; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 6311-35-9, name is 6-Bromonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. name: 6-Bromonicotinic acid

EXAMPLE 31 2-bromo-5-[(2-methylpyrrolidin-1-yl)carbonyl]pyridine The desired product was prepared by substituting 6-bromonicotinic acid for 2-methylnicotinic acid in Example 1. After workup the crude compound was purified by HPLC on C-18 column using a solvent system increasing over 50 minutes in a gradient of 5% to 100% acetonitrile/water containing 0.01% TFA to provide the desired product as the trifluoroacetate salt. MS m/e 268.9 (M+H)+; 1H NMR (DMSO-d6) delta0.86 (d, 0.75H), 1.25 (d, 2.25H), 1.48-1.63 (m, 1H), 1.66-1.80 (m, 1H), 1.81-1.97 (m, 1H), 2.00-2.13 (m, 1H), 3.27-3.37 (m, 0.5H), 3.45-3.54 (m, 1.5H), 3.88-4.00 (m, 0.25H), 4.09-4.21 (m, 0.75H), 7.72 (d, 1H), 7.87 (dd, 1H), 8.52 (d, 1H).

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, 6311-35-9, 6-Bromonicotinic acid.

Reference:
Patent; Haviv, Fortuna; Brandley, Michael F.; Henkin, Jack; US2003/195192; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 83004-10-8, 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. 83004-10-8, name is 2-Bromo-6-(bromomethyl)pyridine, molecular formula is C6H5Br2N, 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 0.050 g (0.169 mmol) of 3-(3,4-dimethyl-benzoyl)-6-fluoro-lH- quinolin-4-one 4tt in 1.0 mL of tetrahydrofuran was added 0.4 mL (0.5 M in toluene, .203 mmol) of potassium hexamethyldisilazide and the reaction solution was stirred for 5 min, followed by the addition of 50.9 mg (0.203 mmol) of 2-bromo-6-bromomethyl-pyridine in 0.5 ml of tetrahydrofuran. The resultant solution was stirred at 60 C for 3 h. The reaction solution was quenched by the addition of water and the aqueous phase was extracted with 3 x 5 mL of ether. The combined organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield 58 mg of l-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4- dimethyl-benzoyl)-6-fluoro-lH-quinolin-4-one 4tt as a yellow solid: LC-MSD, m/z for C24Hi8BrFN2O2, [M+H] = 465.4, 466.5, 467.4, 468.4; Reverse phase HPLC gradient, 20-95% acetonitrile with 0.1% TFA in 4 minutes, retention time = 2.8 min;1H NMR (400 MHz, CDCl3): delta 8.27 (IH, s), 8.12 (IH, m), 7.64 (IH, s), 7.56 (IH, m), 7.51 (IH, m), 7.47 (IH, m), 7.40-7.34 (2H, m), 7.19 (IH, m), 7.00 (IH, m), 5.46 (2H, s), 2.32 (3H, s), 2.31 (3H, s).

According to the analysis of related databases, 83004-10-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2007/59108; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem