Tag: M.W:100-200

Application of 58088-57-6 , The common heterocyclic compound, 58088-57-6, name is Phenyl(pyridin-4-yl)methanamine, molecular formula is C12H12N2, 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 B: Following General Procedure 5-D and using 4-pyridyl-alpha-benzyl amine, the title compound was prepared.

The synthetic route of 58088-57-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Athena Neurosciences, Inc.; Eli Lilly Company; US6506782; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 169205-95-2, 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. 169205-95-2, name is 2-(Methylthio)oxazolo[4,5-b]pyridine, molecular formula is C7H6N2OS, 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.

Step 3: Preparation of 2-morpholinooxazolo[4,5-b]pyridine To a solution of 2-(methylthio)oxazolo[4,5-b]pyridine (2.0g, 12.12 mmol) in THF (5mL) was added morpholine (5mL) and heated at 75 C overnight. The solvent was distilled off to afford the title compound (2.0g, 83.3%). 1HNMR (DMSO-d6, 300MHz): delta 8.20-8.10 (d, 1H), 7.80-7.70 (d, 1H), 7.15-7.00 (m, 1H), 3.75- 3.72 (m, 4H), 3.63-3.52 (m, 4H). LCMS: m/z: 206.5 (M+l) +.

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 169205-95-2, 2-(Methylthio)oxazolo[4,5-b]pyridine.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; GUMMADI, Venkateshwar, Rao; SAMAJDAR, Susanta; WO2015/104688; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 76006-11-6, 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. 76006-11-6, name is 7-Chloro-1H-pyrazolo[3,4-c]pyridine, molecular formula is C6H4ClN3, 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.

Step 2: 7-chloro-2-(difluoromethyl)-2H-pyrazolo[3,4-c]pyridine A mixture of 7-chloro-1H-pyrazolo[3,4-c]pyridine (4.99 g, 32.5 mmol), sodium chlorodifluoroacetate (14.86 g, 97 mmol), and cesium carbonate (40.2 g, 123 mmol) in DMF (81 ml) was heated at 95 C. for 4 h. The reaction was allowed to cool to rt and the solids were filtered. The filtrate was diluted with water and extracted with EtOAc. The organic extract was washed with water, satd NaCl, dried over MgSO4, filtered and concentrated in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (100 g), eluting with a gradient of 5% to 60% EtOAc in hexane, to provide a white solid (1.4117 g, 6.93 mmol, 21.34% yield). MS m/z=203.9 [M+H]+. Calculated for C7H4ClF2N3: 203.

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 76006-11-6, 7-Chloro-1H-pyrazolo[3,4-c]pyridine.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 823-39-2, name is 3,4-Dimethylpyridin-2-amine, the common compound, a new synthetic route is introduced below. Safety of 3,4-Dimethylpyridin-2-amine

Then the solid was stirred with 100 ml ethyl acetate, 150 ml ethanol and 10 ml half concentrated hydrochloric acid. The solvent volume was reduced in vacuo and the precipitate recovered by filtration, washed with diethyl ether and dried over phosphorous pentoxide. 4.97 g (0.021 Mol, 63%) of product was obtained as a white powder. 1H NMR (dDMSO): delta 6.95 ppm (s, 1H), delta 8.02 ppm (s, 1H), delta 8.67 ppm (s, 1H). To prepare 7-butyryloxy-3-carboxy-6-chlorocoumarin, 3.1 g (12.9 mMol) 3-carboxy-6-chloro-7-hydroxycoumarin were dissolved in 100 ml dioxane and treated with 5 ml butyric anhydride, 8 ml pyridine and 20 mg dimethyl aminopyridine at room temperature for two hours. The reaction solution was added with stirring to 300 ml heptane upon which a white precipitate formed. It was recovered by filtration and dissolved in 150 ml ethyl acetate. Undissolved material was removed by filtration and the filtrate extracted twice with 50 ml 1 N hydrochloric acid/brine (1:1) and then brine. The solution was dried over anhydrous sodium sulfate. Evaporation in vacuo yielded 2.63 g (8.47 mMol, 66%) of product. 1H NMR (CDCl3): delta 1.08 ppm (t, 3H, J=7.4 Hz, butyric methyl), delta 1.85 ppm (m, 2H, J1 delta J2=7.4 Hz, butyric methylene), delta 2.68 ppm (t, 2H, J=7.4 Hz, butyric methylene), delta 7.37 ppm (s, 1H, coumarin), delta 7.84 ppm (s, 1H, coumarin), delta 8.86 ppm (s, 1H, coumarin). Preparation of 7-butyryloxy-3-benzyloxycarbonylmethylaminocarbonyl-6-chlorocoumarin is effected as follows.

The synthetic route of 823-39-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Invitrogen Corporation, a Delaware corporation; US2006/8855; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 71670-70-7, name is 2-(Chloromethyl)-5-methylpyridine hydrochloride, the common compound, a new synthetic route is introduced below. Application In Synthesis of 2-(Chloromethyl)-5-methylpyridine hydrochloride

Example 100 l -(3-hydroxybutyl)-3-methyl-7-((5-methylpyridin-2-yl)methyl)-8-(3- (trifl To a solution of l -(3-hydroxybutyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-lH-pur ne- 2,6(3H,7H)- dione (50 mg, 0.121 mmol, intermediate 57) in DMF (3 mL) was added 2- (chloromethyl)-5-methylpyridine hydrochloride (30 mg, 0.182 mmol, intermediate 50), followed by potassium carbonate (50 mg, 0.363 mmol) and TBAI (10mg,0.027mmol). The reaction was stirred at 65 C overnight. The reaction was cooled and partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give a crude product, which was purified by preparative HPLC to give l -(3- hydroxybutyl)-3-methyl-7-((5-methyl^ purine-2,6(3H,7H)-dione (20 mg, 31.9% yield) as white solid. ‘H-NMR (CD3OD) delta 8.319(s,l H), 7.663-7.640(d,l H),7.553-7.510(t,l H), 7.348-7.316(m,3H), 7.233-7.208(m, lH), 5.609(s,2H), 4.1 12-4.004(m,2H), 3.763-3.731(m, l H), 3.457(s,3H), 2.339(s,3H), 1.758- 1 .698(m,2H), 1.197-1.182(d,2H). LCMS retention time 2.714 min; LCMS MH+ 520.

The synthetic route of 71670-70-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HYDRA BIOSCIENCES, INC.; CHENARD, Bertrand; GALLASCHUN, Randall; WO2014/143799; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1346148-32-0, 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. 1346148-32-0, name is Methyl 5-fluoro-3-methylpicolinate. A new synthetic method of this compound is introduced below.

To a solution of 5-fluoro-3-methyl-pyridine-2-carboxylic acid methyl ester (1.28 g) inMeOH (6 ml) was added at 22C a solution of lithium hydroxide mono hydrate (636 mg) in water (3 ml) and stiring was continued for 16 h. The mixture was diluted with water, the MeOH was evaporated at reduced pressure and the pH was adjusted to 1 using 1 N aqueous HC1. The aqueous layer was extracted with AcOEt, the organic layer was dried, evaporated and the residue was crystallized from AcOEt/n-heptane to give the title compound (1.02 g) as a pale yellow solid. MS: m/z = 153.7 [M-H]

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1346148-32-0, Methyl 5-fluoro-3-methylpicolinate, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; SIENA BIOTECH S.P.A.; BANNER, David; GUBA, Wolfgang; HILPERT, Hans; HUMM, Roland; MAUSER, Harald; MAYWEG, Alexander, V.; NARQUIZIAN, Robert; POWER, Eoin; ROGERS-EVANS, Mark; ROMBACH, Didier; WOLTERING, Thomas; WOSTL, Wolfgang; WO2011/138293; (2011); 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. 851386-40-8, name is 4-Chloro-2,5-difluoropyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 4-Chloro-2,5-difluoropyridine

Diisopropylamine (30 g, 0.29 mol) was dissolved in anhydrous tetrahydrofuran (200 ml) and the nitrogen was removed.Cooling to -65 – 40 ,A solution of n-butyllithium / n-hexane (2.5 M, 105 ml)Stir the mixture for 30 minutes.4-chloro-2,5-difluoropyridine (50 g, 0.33 mol) obtained in the above step was slowly added dropwise at -65 C,After the dropwise addition, the mixture was stirred for 1 hour.A solution of methyl iodide (42 g, 0.29 mol)Dripping finished slowly rose to -50 ,And stirred for 1 hour,TLC reaction is complete.The reaction was quenched with saturated ammonium chloride solution,Methyl tert-butyl ether extraction reaction solution,The organic phase was washed with 2N hydrochloric acid,Then washed with water,Saturated sodium bicarbonate wash,Saturated with salt water,The organic phase was separated and dried over anhydrous sodium sulfate,filter,The filtrate was distilled off at 80 C to 120 C under atmospheric pressure,The remaining crude product at 0.09MPa at 70 ~ ~ 100 vacuum distillation of the product,A fraction of 65-80 C was collected to give the product 4-chloro-2,5-difluoro-3-methylpyridine (34.8 g, yield 64%).

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, 851386-40-8, 4-Chloro-2,5-difluoropyridine.

Reference:
Patent; Danuo Pharmaceutical (Suzhou) Co., Ltd.; Ding, Jun; He, Shijie; Zhuang, Zhijun; Ma, Zhenkun; (13 pag.)CN106432222; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 700811-29-6, 2-Chloro-4-hydrazinopyridine, 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, Safety of 2-Chloro-4-hydrazinopyridine, blongs to pyridine-derivatives compound. Safety of 2-Chloro-4-hydrazinopyridine

A microwave reaction vessel was charged with 500 mg of (2-chloro- pyridin-4-yl) -hydrazine (3.48 mmol, 1. 3 equiv) and 848 mg g of N-cyano-N’-(2-phenyl- ISOUREIDO)-BENZENESULFONAMIDE (2.68 mmol, 1 equiv) in a mixture of NMP (5 mL) and diisopropylethylamine (1.4 mL). The sealed vessel was warmed to 220 C for 6 min via microwave irradiation. Upon cooling, the resulting solution was poured onto saturated aqueous sodium hydrogen carbonate (40 mL) and a yellow solid precipitated. The precipitate was collected by vacuum filtration and washed with water (3 X 10 ML). AFTER azeotropic drying (3 x 50 mL of acetonitrile) the dark yellow solid was used without further purification (723.1 mg, 74%); 1H NMR (400 MHz, (CD3) 2SO) 8 9.67 (1H, s), 8. 45 (1H, d, J= 6.3). 7.69 (6H, m), 7.12 (4H, br s); MS (ES) mle 366. 38, (ES) mle 364.49

At the same time, in my other blogs, there are other synthetic methods of this type of compound,700811-29-6, 2-Chloro-4-hydrazinopyridine, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; LEDEBOER, Mark W.; DAVIES, Robert J.; WO2005/13982; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1227594-89-9 ,Some common heterocyclic compound, 1227594-89-9, molecular formula is C6H3F4NO, 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.

[00542] Step C: tert-butyl ethyl(1-((1r,4r)-4-hydroxycyclohexyl)-3-(oxazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (30 mg, 0.07 mmol) was dissolved in THF (0.5 mL). 6-hydroxy-2-methylpyridazin-3(2H)-one (26 mg, 0.21 mmol) and PPh3 (55 mg, 0.21 mmol) were added, followed by DIAD (0.041 mL, 0.21 mmol). The reaction mixture was stirred overnight and then concentrated. The residue was dissolved in DCM (1 mL) and 4N HCl in dioxane (1 mL) was added and stirred for 2 h. The reaction mixture was concentrated and the residue purified on C-18 silica column (5 to 95% ACN in water with 0.1% TFA) to afford N-ethyl-1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-3-(oxazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-amine bis(2,2,2-trifluoroacetate) (17.2 mg, 20% yield). Mass spectrum (apci) m/z = 436.2 (M+H).1H NMR (CD3OD) delta 9.05 (s, 1H), 8.15 (s, 1H), 7.47 (s, 1H), 7.28 (d, J = 9.6 Hz, 1H), 7.00 (d, J = 9.6 Hz, 1H), 6.97 (s, 1H), 5.16 (m, 1H), 4.75 (m, 1H), 3.65 (s, 3H), 3.45 (q, J = 7.2 Hz, 2H), 2.50-2.31 (m, 4H), 1.99-1.86 (m, 4H), 1.38 (t, J = 7.2 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1227594-89-9, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (2019); 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.17282-01-8, name is 3-Bromo-2-fluoro-5-picoline, molecular formula is C6H5BrFN, molecular weight is 190.01, as common compound, the synthetic route is as follows.Safety of 3-Bromo-2-fluoro-5-picoline

Synthesis of Example 9: Intermediate 9a): [Show Image] A flame dried Schlenk flask was charged with 3-bromo-2-fluoro-5-picoline (1.00 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (129 mg), copper(I) iodide (60 mg), and dry N,N-dimethylacetamide (7 ml). The resulting mixture was degassed with atternating vacuum/argon purges. Then 1-tert-butoxycarbonylpiperidin-4-yl)(iodo)zinc (7.37 mmol, prepared as described in above) was added. The mixture was degassed once again and then heated to 80 C overnight. The mainpart of N,N-dimethylacetamide was then evaporated and the remainder was taken up in a mixture of EtOAc and water (100 ml each). The mixture was then filtered through Celite and transferred into a separatory funnel. The phases were separated and the water layer was extracted with EtOAc (3 x 50 ml). The combined organic layer was washed with water and brine (100 ml each), dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by column chromatography to furnish the desired compound in form of a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17282-01-8, 3-Bromo-2-fluoro-5-picoline, and friends who are interested can also refer to it.

Reference:
Patent; Santhera Pharmaceuticals (Schweiz) AG; EP2019100; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem