Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 1122-43-6, 2,6-Dimethyl-3-hydroxypyridine, 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, 1122-43-6, blongs to pyridine-derivatives compound. Safety of 2,6-Dimethyl-3-hydroxypyridine

To a solution of 2,6-dimethyl-3-pyridinol (3 g, 24.35 mmol) in THF (30 ml) at r.t., were added Cs2CO3 (15.87 g, 48.71 mmol) and 3,4-difluoro-l-nitro-benzene (3.87 g, 24.35 mmol). The reaction mixture was heated at reflux for 2 h. After cooling to r.t. the solids were filtered off and the filtrate was evaporated to dryness. The crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2% as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D21 (5.88 g, 92 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1122-43-6, its application will become more common.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; ADDEX PHARMA S.A.; CID-NUNEZ, Jose, Maria; DE LUCAS OLIVARES, Ana, Isabel; TRABANCO-SUAREZ, Andres, Avelino; MACDONALD, Gregor, James; WO2010/130423; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52311-50-9, 2-Chloro-4-ethoxypyridine, 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: 52311-50-9, blongs to pyridine-derivatives compound. SDS of cas: 52311-50-9

To a degassed mixture of 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzamide ( 9.4g, 38 mmol) and 2-chloro-4-ethoxypyridine ( 5g, 31.7 mmol) in dioxane was added Brettphos-prePd (catalytic amount) and CS2CO3 (12.3 g, 37.8 mmol) under N2 atmosphere. The mixture was heated to 100 C and stirred for 3.5 hours. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated, and the residue was purified on silic-gel (PE: EA = 100% ~ 30%) to give N-(4- ethoxypyridin-2-yl)-4-(4,4, 5, 5-tetramethyl- 1 ,3 ,2-dioxaborolan-2-yl)benzamide (8.8 g, yield 75%). 1HNMR (400MHz, CDC13): 5=8.74 (s, 1 H), 8.05-8.02(m, 1 H), 8.01 (s, 1 H), 7.94-7.89 (m, 4 H), 6.60-6.59 (m, 1 H), 4.20-4.14 (m, 2 H), 1.47-1.43 (m, 3 H), 1.36 (s, 12 H), MS (ESI): M/Z (M+l)=369.19.

The synthetic route of 52311-50-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/113932; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 887266-57-1, Adding some certain compound to certain chemical reactions, such as: 887266-57-1, name is 3-Fluoro-2-hydrazinylpyridine,molecular formula is C5H6FN3, 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 887266-57-1.

Under argon, a solution of methyl 2-{3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2- hydroxypropyl] -4,5-dihydro- lH-l,2,4-triazol-1-yl}ethanimidate (Example 2A, 150 mg, 396 muiotaetaomicron) in THF (1.5 ml) was treated at 0C with N,N-diisopropylethylamine (210 mu, 1.2 mmol) and (2S)-1- chloro-1-oxopropan-2-yl acetate (55 mu, 440 muiotaetaomicron) and stirred at 0C for 30 min. 3-Fluoro-2- hydrazinylpyridine (55.4 mg, 436 muiotaetaomicron) was then added and the resulting mixture was stirred overnight at room temperature and evaporated. The residue was purified by preparative HPLC (Method 4) affording 152 mg (67% of th.) of the title compound.LC-MS (Method 1): Rt = 1.01 min; MS (ESIpos): m/z = 570 [M+H]+ -NMR (400 MHz, DMSO-d6) delta [ppm]: 8.46 (br. d, 1H), 8.23-8.05 (m, 1H), 7.88-7.53 (m, 5H), 6.89 (d, 1H), 5.93 (q, 1H), 5.12 (m, 2H), 4.30 (m, 1H), 4.08-3.71 (m, 2H), 1.79 (s, 3H), 1.59 (d, 3H).

According to the analysis of related databases, 887266-57-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; COLLIN-KROePELIN, Marie-Pierre; KOLKHOF, Peter; NEUBAUER, Thomas; FUeRSTNER, Chantal; POOK, Elisabeth; TINEL, Hanna; SCHMECK, Carsten; WASNAIRE, Pierre; SCHIRMER, Heiko; LUSTIG, Klemens; GRIEBENOW, Nils; (195 pag.)WO2019/81302; (2019); 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. 709652-82-4, name is 2-Amino-5-bromonicotinonitrile. A new synthetic method of this compound is introduced below., SDS of cas: 709652-82-4

Boronate 10: Compound 9 (50 g, 0.224 mol), bis(pinacolato)diboron (85.6 g, 0.337 mol), KOAc (44.1 g, 0.449 mol) and Pd(dppf)Cl2.CH2Cl2 (2.77 g, 3.4 mmol) were charged into a flask. Dioxane (400 mL) was added. The reaction mixture was stirred at 100 C. for 2 hr under Ar. When LC-MS indicated that the reaction was completed, the mixture was cooled to room temperature. The mixture was filtered through diatomite, concentrated, diluted with a mixture of ethyl acetate and hexane in 3/1 ratio (1000 mL), filtered through silica gel (300-400 mesh), concentrated, crystallized and dried to give boronate 10 (32 g, 66%) as a white solid.

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, 709652-82-4, 2-Amino-5-bromonicotinonitrile.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; ABUDUSAIMI, Mamuti; YE, Fangguo; SUN, Jiangqin; MIYAMOTO, Hisashi; CHENG, Jay-Fei; OKA, Daisuke; US2014/179675; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 66909-38-4, 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.66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine, molecular formula is C6H7ClN2, molecular weight is 142.5862, as common compound, the synthetic route is as follows.

2-Chloro-4-methyl-5-nitropyridine (lg, 5.8 mmol) was dissolved in EtOH (60 mL). AcOH (4 mL) and Fe (5 eq. ) were added and the mixture was refluxed at 80C overnight. The mixture was filtered through celite and reduced under vacuum to afford the crude 5-amino-2-chloro-4-methylpyridine which was used in the next step with no further purification. The amine was dissolved in cone. HC1 (6 mL), transferred to a 3-neck round bottom flask, and cooled to-5 C. A solution of NaNO2/H2O (440 mgs/5 mL) was slowly added and the mixture was allowed to stir for 10 mins. To a second, separate 3-neck round bottom flask was added H20 (12 mL) and cooled to-5 C. Thionyl chloride (4.5 eq. ) was then added dropwise. After complete addition the mixture was allowed to warm to room temp. Whereupon CuCl (. 05 eq. ) was added and the mixture was then cooled back down to -5C. The first reaction mixture, containing the amine precursor, was slowly added to the second reaction mixture. A froth formed and was filtered off to afford 6-chloro-4-methyl-pyridine-3-sulfonyl chloride which was used in the next step with no further purification. The title compound was synthesized from 2- [2- (R, S)-3-oxo-1, 2,3, 4-tetrahydro-quinoxalin-2-yl]-N- (pyrid- 4-yl) ethyl acetamide and 6-chloro-4-methyl-pyridine-3-sulfonyl chloride using Method G. MS ni/z (M+H) 501.4 ; HPLC (CH3CN-H2O-0.1% TFA): Rt= 2.05 min.

Statistics shows that 66909-38-4 is playing an increasingly important role. we look forward to future research findings about 6-Chloro-4-methylpyridin-3-amine.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2003/93245; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 145255-19-2, 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. 145255-19-2, name is 5-Aminopyridine-2-carboxamide. A new synthetic method of this compound is introduced below.

To a flask charged with 5-aminopyridine-2-carboxamide (48 mg, 0.35 mmol) and DIEA (0.150 mL, 0.861 mmol) in dichloromethane (1 mL) was added a solution of 4-(difluoromethoxy)-2- fluoro-6-[2-(trideuteriomethoxy)-4-(trifluoromethoxy)phenoxy]benzoyl chloride ( 100 mg, 0.231 mmol) in dichloromethane ( 1.5 mL) at 0 C dropwise under an N2 atmosphere. The reaction mixture was stirred for 16 hours at room temperature then diluted with water and extracted with dichloromethane. The organic layer was dried over MgSO/t, filtered and concentrated in vacuo. Silica gel chromatography (0-60% ethyl acetate/hexanes) provided 5-[[4-(difluoromethoxy)-2-fluoro-6-[2-(trideuteriomethoxy)-4- (trifluoromethoxy)phenoxy]benzoyl]amino]pyridine-2-carboxamide (22 mg, 18%). ESI-MS m/z calc. 534.10, found 535.2 (M+l)+; retention time (Method B): 1.67 minutes (3 minute run). ‘H NMR (400 MHz, DMSO-d6) 5 11.18 (s, 1H), 8.85 (dd, J = 2.5, 0.7 Hz, 1H), 8.25 (dd, J = 8.6, 2.5 Hz, 1H), 8.08 – 7.97 (m, 2H), 7.60 – 6.93 (m, 6H), 6.37 (t, J = 1.7 Hz, 1H) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,145255-19-2, 5-Aminopyridine-2-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; AHMAD, Nadia; ANDERSON, Corey; ARUMUGAM, Vijayalaksmi; ASGIAN, Iuliana, Luci; CAMP, Joanne, Louise; FANNING, Lev Tyler, Dewey; HADIDA RUAH, Sara, Sabina; HURLEY, Dennis; SCHMIDT, Yvonne; SHAW, David; SHETH, Urvi, Jagdishbhai; THOMSON, Stephen, Andrew; (691 pag.)WO2019/14352; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 185315-53-1 ,Some common heterocyclic compound, 185315-53-1, molecular formula is C6H5Cl2N, 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.

General procedure: A mixture of N-tert-butyl-7-(3,3-difluoropyrrolidin-l-yl)-3H-triazolo[4,5-d]pyrimidin-5- amine (25 mg, 0.08 mmol), NEt3 (14.6 mg, 0.144 mmol) and l-(bromomethyl)-2- (trifluoromethyl)benzene (26.8 mg, 0.112 mmol) in 2 mL DMF was stirred at room temperature for 5 h. The mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt . After evaporation of the product containing fractions 5.2 mg (14 %) of the title compound was isolated. MS(m/e): 456.4 (MH+). Example 24; N-tert-Butyl-3-[(3-chloropyridin-2-yl)methyl]-7-(3,3-difluoropyrrolidin-l-yl)triazolo [4,5-d]pyrimidin-5-amine; In analogy to the procedure described for the synthesis of N-tert-butyl-7-(3,3- difluoropyrrolidin- l-yl)-3-[[2- (trifluoromethyl)phenyl] methyl] triazolo [4, 5 -d] pyrimidin- 5 – amine (example 22) the title compound was prepared from N-tert-butyl-7-(3,3- difluoropyrrolidin-l-yl)-3H-triazolo[4,5-d]pyrimidin-5-amine and 3-chloro-2- (chloromethyl)pyridine. MS(m/e): 423.3 (MH+).

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. 185315-53-1, 3-Chloro-2-(chloromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ROEVER, Stephan; ROGERS-EVANS, Mark; NETTEKOVEN, Matthias; SCHMITT, Sebastien; GRETHER, Uwe; KIMBARA, Atsushi; WO2015/32769; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 22280-60-0, 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 22280-60-0, name is 6-Chloro-2-methyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

6-methoxy-3-nitro-2-picoline 0.46 gm (20 mMol) sodium were dissolved in 15 mL anhydrous methanol. To this solution were added 2.3 gm 6-chloro-3-nitro-2-picoline in portions. The resulting mixture was stirred for 18 hours at room temperature and then 1 hour at reflux. The reaction mixture was poured into 100 mL of ice water with vigorous stirring. The suspension was filtered and the solid dried at 30C under reduced pressure for 18 hours to provide 2.04 gm (91%) of the desired compound as a tan solid.

According to the analysis of related databases, 22280-60-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; EP875513; (1998); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 72587-18-9, 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 72587-18-9, name is 2-Chloro-5-(trifluoromethyl)pyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows.

N-[2-Chloro-5-(trifluoromethyl)pyridin-3-yl]-3-(ethylsulphanyl)imidazo[1,2-a]pyridine-2-carboxamide (XXVI-1) 1.1 mg (9.37 mmol) of thionyl chloride were added dropwise to a solution of 298 mg (1.33 mmol) of 3-(ethylsulphanyl)imidazo[1,2-a]pyridine-2-carboxylic acid in 10 ml of acetonitrile, and the mixture was heated under reflux for 3 h. The solvent was removed under reduced pressure and the residue was twice co-evaporated with toluene. The residue was dissolved in 3 ml of N,N-dimethylformamide. Separately, 263 mg (1.33 mmol) of 2-chloro-5-(trifluoromethyl)pyridine-3-amine were added to a suspension at 0 C., of 107 mg (2.67 mmol) of sodium hydride in 7 ml of N,N-dimethylformamide, and the mixture was stirred for another 30 min. The acid chloride solution prepared beforehand was then slowly added dropwise at 0 C. The reaction mixture was stirred at room temperature for a further 2 h. The mixture was poured onto ice-water and extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate and the solvent was then removed. The crude product was purified by HPLC using a water/acetonitrile gradient as mobile phase. (log P (neutral): 4.39; MH+: 401; 1H-NMR (400 MHz, D6-DMSO) delta ppm: 1.09 (t, 3H), 2.98 (q, 2H), 7.22-7.25 (m, 1H), 7.55-7.60 (m, 1H), 7.82 (d, 1H), 8.66 (d, 1H), 8.73 (d, 1H), 9.07 (d, 1H).

According to the analysis of related databases, 72587-18-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FISCHER, Ruediger; WILCKE, David; HAGER, Dominik; ILG, Kerstin; EILMUS, Sascha; GOeRGENS, Ulrich; TURBERG, Andreas; (71 pag.)US2018/116222; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1122-61-8, 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. 1122-61-8, name is 4-Nitropyridine. A new synthetic method of this compound is introduced below.

General procedure: A solution of complex 4a (1 g, 4.25 mmol) in benzene (10 ml) was stirred at 15-20 and treated with a solution of heterocyclic amine or oxaadamantane () (4.25 mmol) in benzene (5 ml) (Scheme 10, Table 1). The reaction mixture was stirred for the indicated time at room temperature, with periodic control of the amount of evolved THF by GLC (60-70, adsorbent – chromosorb, liquid phase – PEG monolaurate). After the increase of THF signal stopped, the reaction mixture was evaporated from Petri dish under exaust hood, the residue was extracted first with hexane and then with Et2O. The combined extract was evaporated under vacuum at room temperature, the residue was recrystallized from Et2O-hexane mixture. Complexes of trinitromethylborane with amines (compounds 7-s) or with oxaadamantanes (compounds 4d,e) were thus obtainecharacteristics, as well as yields and melting points of target complexes 4d,e and 7-s are given in Table 1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1122-61-8, its application will become more common.

Reference:
Article; Shitov; Tartakovskii; Ioffe; Chemistry of Heterocyclic Compounds; vol. 50; 12; (2015); p. 1647 – 1657; Khim. Geterotsikl. Soedin.; vol. 50; 12; (2014); p. 1795 – 1806,12;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem