Tag: M.W:200-300

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. 142266-62-4, name is 2,5,6-Trichloronicotinamide. A new synthetic method of this compound is introduced below., Quality Control of 2,5,6-Trichloronicotinamide

To a mixture of 2,5,6-trichloronicotinamide (Intermediate P; 1.4 g, 6.1 mmol) in THF (12 mL) was added oxalyl chloride, 2 M solution in DCM (3.3 mL, 6.5 mmol) at rt and the mixture was stirred and heated at 65 C. for 3 h. The mixture was cooled to 0 C. To the cooled mixture was added a solution of 1,4-diisopropyl-1H-pyrazol-5-amine (Intermediate 161; 1.03 g, 6.13 mmol) in THF (5 mL) and the mixture was stirred at rt for 15 h. The reaction mixture was quenched with satd NaHCO3 (100 mL), extracted with EtOAc (2*50 mL), washed with brine (1*50 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography (eluent: 0-50% EtOAc-EtOH (3:1)/heptane) to provide 2,5,6-trichloro-N-((1,4-diisopropyl-1H-pyrazol-5-yl)carbamoyl)nicotinamide (2.43 g, 5.79 mmol, 94% yield) as orange syrup. 1H NMR (400 MHz, DMSO-d6) delta 11.36 (br s, 1H), 9.39 (br s, 1H), 8.63 (s, 1H), 7.33 (s, 1H), 4.37 (dt, J=13.3, 6.6 Hz, 1H), 2.64-2.75 (m, 1H), 1.33 (d, J=6.4 Hz, 6H), 1.13 (d, J=7.0 Hz, 6H), m/z (ESI, +ve ion): 417.6 (M+H)+.

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, 142266-62-4, 2,5,6-Trichloronicotinamide.

Reference:
Patent; Amgen Inc.; ALLEN, John Gordon; LANMAN, Brian Alan; CHEN, Jian; REED, Anthony B.; CEE, Victor J.; LIU, Longbin; LOPEZ, Patricia; WURZ, Ryan Paul; NGUYEN, Thomas T.; Booker, Shon; ALLEN, Jennifer Rebecca; CHU-MOYER, Margaret; AMEGADZIE, Albert; CHEN, Ning; GOODMAN, Clifford; LOW, Jonathan D.; MA, Vu Van; MINATTI, Ana Elena; NISHIMURA, Nobuko; PICKRELL, Alexander J.; WANG, Hui-Ling; SHIN, Youngsook; SIEGMUND, Aaron C.; YANG, Kevin C.; TAMAYO, Nuria A.; WALTON, Mary; XUE, Qiufen; US2019/374542; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1004294-58-9, 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 1004294-58-9, name is 6-Bromo-5-chloropyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

Di-tert-butyl dicarbonate (19 g, 87 mmol) was added to a stirring mixture of 6-bromo-5-chloro-2-pyridinamine (8.6 g, 42 mmol, from Step 1), dichloromethane (83 mL), and N,N-diisopropylethylamine (22 mL, 120 mmol) at room temperature under a nitrogen atmosphere. After 14 h, 4- (dimethylamino)pyridine (0.51 g, 4.2 mmol) was added. After an additional 3 h, the reaction mixture was concentrated under a vacuum, and the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was isolated, and was washed sequentially with saturated aqueous sodium bicarbonate and brine, dried (sodium sulfate), filtered, and concentrated under a vacuum. The residue was dissolved with dichloromethane, silica gel (40 g) was added to the solution, and the volatiles were removed under a vacuum. The residue was subjected to flash chromatography on silica gel (9: 1 hexane- ethyl acetate). The isolated material was dissolved with dichloromethane, silica gel (20 g) was added to the solution, and the volatiles were removed under a vacuum. The residue was subjected to flash chromatography on silica gel (19: 1 hexane-ethyl acetate) to give di-tert-butyl (6-bromo-5-chloro-2- pyridinyl)imidodicarbonate (6.3 g) as a colorless solid.

According to the analysis of related databases, 1004294-58-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael D.; BOURBEAU, Matthew Paul; CROGHAN, Michael D.; FOTSCH, Christopher H.; HUNGATE, Randall W.; KONG, Ke; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis D.; REICHELT, Andreas; SIEGMUND, Aaron C.; TADESSE, Seifu; ST. JEAN, David Jr; YANG, Kevin C.; YAO, Guomin; WO2013/173382; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 171178-45-3, 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. 171178-45-3, name is tert-Butyl (6-chloropyridin-3-yl)carbamate, molecular formula is C10H13ClN2O2, 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.

(c) 5-(tert-Butoxycarbonyl)-2-chloroisonicotinic acid. To a solution of tert-butyl 6-chloropyridin-3-ylcarbamate (1O g, 0.045 mol) and N, N, N’, N’-tetramethyleethylenediamine (20 mL) in dry Et2O (200 mL) was added n- BuLi (2.5 M solution in hexanes, 84 mL) dropwise with stirring at -78C. After the addition, the reaction mixture was warmed to -15C and stirred at the same temperature for 2 hours. The mixture was cooled to -78C and CO2 gas was bubbled into the reaction solution at -78C for 1 hour. The reaction mixture was then stirred at room temperature overnight, cooled to 0C and quenched with water. The pH of the aqueous phase was adjusted to pH=3 with IN hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over anhydrous MgSO4, and filtered. The filtrate was evaporated under reduced pressure, and the residue was dried in vacuo to give the title compound.

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 171178-45-3, tert-Butyl (6-chloropyridin-3-yl)carbamate.

Reference:
Patent; AMGEN INC.; WO2008/76425; (2008); 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.58584-86-4, name is Ethyl 2,6-dichloronicotinate, molecular formula is C8H7Cl2NO2, molecular weight is 220.05, as common compound, the synthetic route is as follows.Recommanded Product: 58584-86-4

(a) Ethyl6-{4-[(benzylsulfonyl)carbamoyl]piperidin-1-yl}-2-chloronicotinate A micro wave vial was charged with DIPEA (2.73 g, 21.1 mmol), ethyl2,6-dichloronicotinate (Example 43(a)) (1.547 g, 7.03 mmol), N-(benzylsulfonyl)piperidine-4-carboxamide (Example 6(d)) (2.28 g, 8.08 mmol) and DMF and the mixture was heated to 120 C. for 10 minutes followed by 150 C. for 10 minutes using microwave single node heating. Ratio of the two possible regioisomers was ca. 1:1 together with some bis-addition adduct. The crude product was purified by first using HPLC (Kromasil C8, 10 mum, using a gradient of MeCN with an acidic second eluent (H2O/MeCN/AcOH, 95/5/0.1)) followed by flash chromatography using a stepwise gradient of heptane/EtOAc 1/1 then heptane/EtOAc 1/1+0.15% FA and finally heptane/EtOAc 1/2+0.15% FA. (Rf product (heptane/EtOAc 1/2+0.15% FA)=0.47) to give ethyl6-{4-[(benzylsulfonyl)carbamoyl]piperidin-1-yl}-2-chloronicotinate. Yield: 610 mg (19%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58584-86-4, Ethyl 2,6-dichloronicotinate, and friends who are interested can also refer to it.

Reference:
Patent; AstraZeneca AB; US2008/171732; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 885276-93-7 ,Some common heterocyclic compound, 885276-93-7, molecular formula is C10H9BrN2O2, 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.

Synthesis of fR)-ethyl 5-(2-(3-cvano-5-fluoroDhenyl)-4A-difluoroDyrrolidin-1- yl)pyrazolo[1,5-alpyridine-3-carboxylate (X-8)[000304] A N2 purged flask was charged with ethyl 5-bromopyrazolo[1 ,5-a]pyridine-3- carboxylate (100 mg, 0.37 mmol), palladium acetate (1 .7 mg, 7 muiotaetaomicronIota), xantphos (7 mg, 1 1 muiotaetaomicronIota), cesium carbonate (170 mg, 0.52 mmol), 1 ,4-dioxane (0.5 ml_) and (R)-3- (4,4-difluoropyrrolidin-2-yl)-5-fluorobenzonitrile (I-24) (84 mg, 0.37 mmol). The contents were heated to 140 C for 1 hour under microwave irradiation. Upon cooling to room temperature the reaction was partitioned with EtOAc and water. The organic layer was washed with water, brine, dried over magnesium sulfate, filtered and reduced to dryness. The crude product was purified by column chromatography on silica gel with EtOAc/hexanes gradient as eluant to yield (R)-ethyl 5-(2-(3-cyano-5- fluorophenyl)-4,4-difluoropyrrolidin-1 -yl)pyrazolo[1 ,5-a]pyridine-3-carboxylate (X-8). 1 H NMR (400MHz, CDCI3) delta 8.26 (d, J = 7.6 Hz, 1 H), 8.24 (s, 1 H), 7.38 (s, 1 H), 7.33 – 7.29 (m, 1 H), 7.25 -7.21 (m, 1 H), 6.93 (d, J = 2.8 Hz, 1 H), 6.19 (dd, J = 2.8, 7.6 Hz, 1 H), 5.14 (dd, J = 4.4, 9.2 Hz, 1 H), 4.34 – 4.25 (m, 2 H), 4.25 – 4.16 (m, 1 H), 4.05 – 3.93 (m, 1 H), 3.14 – 2.98 (m, 1 H), 2.53 – 2.42 (m, 1 H), 1 .34 (t, J = 7.2 Hz, 3 H). MS m/z 415.1 (M+1 )+.

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. 885276-93-7, Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IRM LLC; MOLTENI, Valentina; FAN, Yi; LOREN, Jon; SMITH, Jeffrey M.; FLATT, Brenton T.; WO2012/116217; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 159981-19-8, 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. 159981-19-8, name is 6-(2,2,2-Trifluoroethoxy)nicotinaldehyde, molecular formula is C8H6F3NO2, 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.

n-Butyllithium (5.14 mL, 13.4 mmol) is added to a suspension of methyltriphenylphosphonium bromide (4.41 g, 12.34 mmol) in tetrahydrofuran (51 mL) at -78 oC under nitrogen atmosphere . The reaction mixture is warmed to room temperature to yield deep red ylide solution. To ylide solution, cooling in ice, is introduced 6-(2,2,2-trifluoroethoxy)nicotinaldehyde (2.11 g, 10.3 mmol, Step-1) in tetrahydrofuran (10 mL) and stirred at room temperature for 3 hours. The reaction mixture is poured into water, extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane / ethyl acetate (10:1) to give 1.56 g (75% yield) of the title compound as colorless oil.1H-NMR (300 MHz, CDCl3) delta 8.10 (1H, d, J = 2.6 Hz), 7.75 (1H, dd, J = 8.4, 2.6 Hz), 6.84 (1H, d, J = 8.4 Hz), 6.65 (1H, dd, J = 17.6, 11.0 Hz), 5.68 (1H, d, J = 17.6 Hz), 5.27 (1H, d, J = 11.0 Hz), 4.76 (2H, q, J = 8.4 Hz), MS (ESI) m/z: 204 (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 159981-19-8, 6-(2,2,2-Trifluoroethoxy)nicotinaldehyde.

Reference:
Patent; RAQUALIA PHARMA INC.; YAMAGISHI, Tatsuya; KAWAMURA, Kiyoshi; ARANO, Yoshimasa; MORITA, Mikio; WO2012/53186; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13534-90-2, 3,4-Dibromopyridine, 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, 13534-90-2, blongs to pyridine-derivatives compound. Computed Properties of C5H3Br2N

The titled compound was prepared by the reaction of 3,4-dibromopyridine (1.01 g, 4.26 mmol) with 4-nitrophenylboronic acid pinacol ester (1.06 g, 4.26 mmol) using cesium carbonate (2.07 g, 6.39 mmol) and [l, -bis(diphenylphosphino)ferrocene]dichloropalladium (II) (155 mg, 0.21 mmol) in a mixture of DMSO and water (20 mL, 3: 1) as per the procedure described in Step 1 of Intermediate 1 to yield 455 mg of the product; 1H NMR (300 MHz, CDC13) delta 7.33 (d, 7 = 4.8 Hz, 1H), 7.63 (d, 7 = 8.7 Hz, 2H), 8.35 (d, 7 = 8.7 Hz, 2H), 8.64 (d, 7 = 5.1 Hz, 1H), 8.89 (s, 1H) ; ESI-MS (m/z) 281 (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,13534-90-2, its application will become more common.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; DAS, Sanjib; GHARAT, Laxmikant Atmaram; HARDE, Rajendra Laxman; SHELKE, Sandeep Yadunath; PARDESHI, Shailesh Ramesh; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; BAJPAI, Malini; (181 pag.)WO2017/21879; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1123194-98-8 ,Some common heterocyclic compound, 1123194-98-8, molecular formula is C10H10BrN3O, 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.

Synthesis of (E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylamide Triethylamine (52 ml) was added to a suspension of 6-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine (49.8 g), tris(dibenzylideneacetone)dipalladium (0) (5.11 g), tri-o-tolylphosphine (3.41 g) and acrylamide (14.5 g) in N,N-dimethyl formamide (260 ml). The reaction solution was stirred at 100C for 50 minutes. The reaction solution was returned to room temperature and then filtered through celite. The filter cake was sequentially washed with N,N-dimethylformamide, methanol, a 50% N,N-dimethylformamide solution and N,N-dimethylformamide. The resulting filtrate was filtered through celite again, and the filtrate was concentrated under reduced pressure. Toluene was added to the residue, and the reaction solution was concentrated again. Toluene and a saturated sodium bicarbonate solution were added to the resulting residue, and the insoluble matter was collected by filtration. The resulting powder was dried under reduced pressure to obtain 42.96 g of the title compound. The property values of the compound are as follows. 1H-NMR (CDCl3) delta (ppm): 2.30 (d, J=0.8Hz, 3H), 4.07 (s, 3H), 5.57 (brs, 1H), 5.68 (brs, 1H), 6.98 (brs, 1H), 7.00 (d, J=15.2Hz, 1H), 7.06 (d, J=7.6Hz, 1H), 7.54 (d, J=7.6Hz, 1H), 7.56 (d, J=15.2Hz, 1H), 7.82 (d, J=1.2Hz, 1H). ESI-MS; m/z 259 [M++H].

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. 1123194-98-8, 6-Bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2181992; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5349-17-7, 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide, 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, 5349-17-7, blongs to pyridine-derivatives compound. COA of Formula: C7H7Br2NO

(c) Preparation of [(2-chloro-6-nitrophenyl)methyl](4-(4-pyridyl)(1,3-thiazol-2-yl))amine.To a solution of N-({[(2-chloro-6-nitrophenyl)methyl]amino}thioxomethyl)benzamide (Step b) (1.22 g, 3.5 mmol) in 70% aqueous MeOH (50 ML) was added K2CO3 (567 mg, 4.1 mmol) and the reaction was heated to reflux.After 1.5 h, the reaction was cooled (40 C.) and 2-bromo-1-(4-pyridyl)ethan-1-one hydrobromide (992.4 mg, 3.5 mmol) was added.After 1.5 h, the reaction mixture was cooled to RT and purified by flash chromatography with hexanes:EtOAc:CH2Cl2:MeOH (9:1:0:0, 3:1:0:0, 1:1:0:0, 0:0:49:1) as eluant to afford an off-white amorphous solid. MS m/z: 347 (M+1); 345 (M-1). Calc’d for C15H11ClN4O2S-b 346.03.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5349-17-7, its application will become more common.

Reference:
Patent; Huang, Qi; Kaller, Matthew; Nguyen, Thomas; Norman, Mark H.; Rzasa, Robert; Wang, Hui-Ling; Zhong, Wenge; US2003/229068; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 183741-80-2, tert-Butyl (6-methoxypyridin-3-yl)carbamate, 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, 183741-80-2, blongs to pyridine-derivatives compound. Formula: C11H16N2O3

[0614] Procedure: To a stirred solution of tert-butyl (6-methoxypyridin-3-yl)carbamate (7 g, 31.231 mmol) and tetramethylethylenediamine (14.05 mL , 93.640 mmol) in ether (140 mL) was added n-BuLi (46.82 mL, 3 eq, 2M solution in cyclohexane) at -78 C and the mixture was stirred at-10 C for 3 h. After re-cooling to- 78 C, dry carbon dioxide gas was bubbled and stirred for 5 min. The resulting suspension was allowed to room temperature and diluted with water. Organic layer separated and washed with dil. ammonium hydroxide solution. The combined aq. layer was acidified to pH 6 with dil. HCl. The resulting precipitate was filtered, dried under vacuum to afford 5-((tert-butoxycarbonyl)amino)-2-methoxyisonicotinic acid as off white solid (7.2 g, 85.99 %).1HNMR (400 MHz, DMSO-d6): delta 9.37 (bs, 1H), 8.67 (s, 1H), 7.11-(s, 1H), 3.84 (s, 3H), 1.44 (s, 9H). LC-MS (ES) m/z = 269.1 [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,183741-80-2, its application will become more common.

Reference:
Patent; MAVUPHARMA, INC.; GALLATIN, William Michael; ODINGO, Joshua; DIETSCH, Gregory N.; FLORIO, Vincent; VENKATESHAPPA, Chandregowda; DURAISWAMY, Athisayamani Jeyaraj; (273 pag.)WO2019/46778; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem