Tag: M.W:100-200

Application of 1403899-44-4 ,Some common heterocyclic compound, 1403899-44-4, molecular formula is C9H11ClN2, 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.

Alternative procedure: Potassium teit-butoxide (600 mg, 5.36 mmol) was added to a stirred solution of 6-chloro-3,3-dimethyl-2,3-dihydro-1 H-pyrrolo[3,2-c]pyridine (800 mg, 4.38 mmol) in anhydrous THF (15 mL) and the mixture was stirred at room temperature for 10 minutes. Asolution of di-teit-butyl dicarbonate (1.07 g, 4.89 mmol) in anhydrous THF (15 mL) was added and the mixture was stirred at room temperature overnight. The organic solvent was removed in vacuo, the aqueous residues were diluted with water (100 mL) and extracted with EtOAc (2 x 200 mL). The organic layers were combined and the solvent was removed in vacuo to afford the title compound (1.19g, 96%), NMR data consistent with those previouslyobtained.

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. 1403899-44-4, 6-Chloro-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; CHESSARI, Gianni; JOHNSON, Christopher Norbert; PAGE, Lee William; MILLEMAGGI, Alessia; HOWARD, Steven; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; WO2014/60768; (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. 167837-43-6, name is (E)-3-(6-Aminopyridin-3-yl)acrylic acid, molecular formula is C8H8N2O2, 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. Formula: C8H8N2O2

EDC (231 mg, 1.2 mmol) was added to a solution of (E)-3- (6-AMINO-PYRIDIN-3- yl) acrylic acid (164 mg, 1.0 mmol), methyl- (3-methyl-benzofuran-2-ylmethyl) amine (193 mg, 1.1 mmol), HOBTNo.H2O (149 mg, 1.1 mmol) and DIPEA (525 PL, 3.0 mmol) in dry DMF (10 mL). After 18 hr of stirring, the mixture was diluted with water (60 mL) and extracted with EtOAc (2X20 mL). The oraganic layer was washed with brine (2 x 30 mL), dried and evaporated. Flash chromatography (silica 1-3% MEOH in CH2Cl2) of the residue furnished pure free base which was dissolved in CH2C12 (10 mL). After addition OF HCL (1.5 mL, 1M in ether), the solvents were evaporated, washed with ether and dried to afford the title compound (195 mg, 54%). 1H NMR (300 MHz, DMSO-d6) 8 8.36 (m, 3H), 7.50 (m, 3H), 7.25 (m, 3H), 7.02 (m, 1H), 4.98 and 4.79 (rotamers, 2s, 2H), 3.17 and 2.92 (rotamers, 2s, 3H), 2.26 (s, 3H). MS (ESI) nile 322 (M+H) +.

With the rapid development of chemical substances, we look forward to future research findings about 167837-43-6.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2004/52890; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 121643-44-5, 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. 121643-44-5, name is 2-Methoxy-3-(trifluoromethyl)pyridine, molecular formula is C7H6F3NO, 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 2-methoxy-3-(trifluoromethyl)pyridine (20.0 g, 1 13.0 mmol) and 1 ,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (43.6 g, 152.0 mmol) was added TFA (80 ml_) and the resulting mixture stirred at rt for 8h under argon. The TFA was removed in vacuo (50 mbar, 45C) and the residue suspended in tert-butyl methyl ether (200 ml_). The resultingcolourless solid was removed by filtration and washed with tert-butyl methyl ether (50 mL). The filtrate was concentrated in vacuo and suspended in EtOAc (50 mL) The insoluble colourless solid was removed by filtration and washed with EtOAc (50 mL).The filtrate was concentrated in vacuo, diluted with heptane/ tert-butyl methyl ether (5/1 , 20 mL) and the insoluble colourless solid was removed by filtration. The filtrate was purified by column chromatography on silica gel with heptane / EtOAc, 100/0 to 90/10. The crude product was filtered through a plug of NaHC03 (20g) and the filtrate evaporated in vacuo to give a golden oil (27.9 g). The oil was dissolved in heptanes (20 mL) and purified by filtered through a plug of silica gel (80 g), eluting with heptane to give 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine as a colourless oil (22.5g, 74% yield).1H-NMR (400 MHz, DMSO-d6,298 K): delta ppm 4.03 (s, 3H) 7.95 (d, 1 H) 8.4 (d, 1 H).

According to the analysis of related databases, 121643-44-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2013/88404; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 113293-70-2, 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. 113293-70-2, name is 2,6-Dichloroisonicotinaldehyde. A new synthetic method of this compound is introduced below.

To a solution of 2,6-dichloroisonicotinaldehyde (30 g, 170 mmol) in dichloromethane (450 mL) was added diethylaminosulfur trifluoride (90 mL, 682 mmol) in dichloromethane (200 mL) at -78 C. over 10 minutes. The reaction mixture was warmed to 25 C. and stirred for 2 hours. The reaction mixture was quenched with ice water (500 mL) and extracted with dichloromethane (3 × 300 mL). The combined organic layers were washed with NaHCO 3 (saturated aqueous solution, 200 mL), water (200 mL) and brine (200 mL), dried over Na 2 SO 4, filtered and concentrated to give the desired product (20 g, 57% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113293-70-2, its application will become more common.

Reference:
Patent; Abbvie Incorporated; Argiriadi, Maria A.; Breinlinger, Eric C.; Chien, Ellen Yulin Tsai; Cowart, Marlon D.; Frank, Kristine E.; Friedman, Michael M.; Hardy, David J.; Herold, J. Martin; Liu, Huaqing; Chu, Wei; Scanio, Marc J.; Schrimpf, Michael R.; Vargo, Thomas R.; Van Epps, Stacy A.; Webster, Matthew P.; Little, Andrew J.; Dunstan, Teresa A.; Katcher, Matthew H.; Schedler, David A.; (232 pag.)JP6557436; (2019); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 65515-39-1, 2-Methoxy-4,6-dimethylnicotinonitrile, 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, 65515-39-1, blongs to pyridine-derivatives compound. SDS of cas: 65515-39-1

Add a I M solution of DIBAL-H in toluene (240 mL, 240 mmol) to a solution of 2-methoxy-4,6-dimethyl-pyridine-3-carbonitrile (48 g, 295.95 mmol) in DCM (480 mL)at 0 C over 2 hr. Remove the ice bath after 1 hr and stir at RT overnight. Cool in a waterbath at RT and quench by slowly adding a mixture of lMaqueous HC1 (192 mL) andAcOH (192 mL). Add DCM, separate the layers, wash the organic phase with saturated aqueous NaC1, dry over Na2504, filter and concentrate in vacuo. Subject the resulting residue to chromatography on silica, eluting with a gradient of 0-20% EtOAc/hexane to afford title compound as a solid (22.6 g, 46% yield) after solvent evaporation. ES/MS(mlz): 166 (M+H). ?H NMR (400.1 MHz, CDC13) oe 2,43 (s, 3H), 2.54 (s, 3H), 4.01 (s,3H), 6.61 (s, 1H), 10.48 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,65515-39-1, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; DOMINGUEZ, Esteban; GUO, Deqi; MADER, Mary Margaret; NGUYEN, Anh-Quan Hannah; DEL PRADO, Miriam Filadelfa; RICHETT, Michael Enrico; RODRIGUEZ, Michael John; YIP, Yvonne Yee Mai; YU, Kuo-Long; (165 pag.)WO2017/35060; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 22918-01-0, Adding some certain compound to certain chemical reactions, such as: 22918-01-0, name is 2-Bromo-4-chloropyridine,molecular formula is C5H3BrClN, 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 22918-01-0.

To a solution of 2-bromo-4-chloropyridine (1.6 g, 8.0 mmol) in anhydrous tetrahydrofuran (40 mL) cooled at -70 C. was added the solution of lithium diisopropyl-amide (5.0 mL, 10.0 mmol, 2.0 M) over a period of 5 minutes and stirred at -70 C. for another 1 h. Anhydrous DMF (1.3 g) was introduced over a period of 3 minutes and the mixture was stirred for another 30 minutes. It was then quenched with saturated NH4Cl (30 mL) and extracted with ethyl acetate (20 mL*3). The combined organic layer was dried over anhydrous Mg2SO4, filtered, and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (20:1) to afford 114a as a yellow solid (900 mg, 48%). 1H NMR (500 MHz, DMSO) delta 10.21 (s, 1H), 8.52 (d, J=5.5 Hz, 1H), 7.79 (d, J=5.0 Hz, 1H).

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. 22918-01-0, 2-Bromo-4-chloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Young, Wendy B.; US2013/116262; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 61494-55-1, 2-(2-Chloropyridin-3-yl)acetic acid, 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, Recommanded Product: 2-(2-Chloropyridin-3-yl)acetic acid, blongs to pyridine-derivatives compound. Recommanded Product: 2-(2-Chloropyridin-3-yl)acetic acid

[0540] To a stirred solution of diisopropyl amine (0.82 mL, 5.8 mmol) in anhydrous THF (5 mL) cooled to -15C was added n-butyl lithium (2.5 M in hexanes, 2.3 mL, 5.8 mmol) slowly, maintaining the temperature of the flask between -10C and 0C. The resultant mixture was stirred at room temperature for 15 minutes before being cooling to 0C. The LDA thus formed was added to a rapidly stirred suspension of 2-(2-chloropyridin-3-yl)acetic acid (500 mg, 2.9 mmol) in anhydrous THF (10 mL) at 0C. The resultant bright yellow suspension was stirred at 0C for 15 min. A solution of 2-fluoro-4-iodo-l -isothiocyanatobenzene (814 mg, 2.9 mmol) in anhydrous THF (10 mL) was then added to the reaction mixture (brown suspension) and heated to 65C for 18 hours. The reaction mixture was cooled and the volatiles removed in vacuo. The resultant crude product was redissolved in THF, cooled to 0C and 10% aqueous acetic acid in water (10 mL) was added slowly. Acetonitrile (5 mL) was added slowly until a brown solid developed, the solid was isolated by filtration and washed with ether and acetonitrile to give the title compound. LC/MS: [M+l]+ 415; NMR (300 MHz, DMSO-d6): d 10.74 (s, 1H), 9.21 (s, 1H), 8.36-8.25 (m, 2H), 7.79 (d, J = 1.8 Hz, 1H), 7.68-7.61 (m, 1H), 7.51 (t, J=8.5 Hz, 1H), 7.42- 7.31 (m, 1H).

The synthetic route of 61494-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NFLECTION THERAPEUTICS, INC.; TSAI, Kenneth, Y.; KINCAID, John; SARIN, Kavita, Yang; (319 pag.)WO2020/106303; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1206981-49-8 ,Some common heterocyclic compound, 1206981-49-8, molecular formula is C6H5F3N2O, 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.

To a solution of 3-(trifluoromethoxy)pyridin-2-amine (300 mg, 1.68 mmol) in dichloromethane (8 mL) was added N-bromosuccinimide (450 mg, 2.53 mmol) at 20 C. The reaction mixture was stirred at the same temperature for another 5 min and subsequently concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 15% ethyl acetate in petroleum ether) affording product (220 mg, 51%): 1H NMR (400 MHz, DMSO-d6) delta 8.03 (d, J=2.0 Hz, 1H), 7.75-7.74 (m, 1H), 6.68 (brs, 2H).

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. 1206981-49-8, 3-(Trifluoromethoxy)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; Siu, Michael; Estrada, Anthony; Liu, Wen; Lyssikatos, Joseph P.; Patel, Snahel; Liang, Guibai; Chen, Kevin; US2015/175619; (2015); 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.72141-44-7, name is 4-Chloro-2-methoxypyridine, molecular formula is C6H6ClNO, molecular weight is 143.5709, as common compound, the synthetic route is as follows.Formula: C6H6ClNO

To a solution of LDA (1.0 M solution in hexane) (29.3 mL, 29.3 mmol) in THF (45 mL) was added a solution of 4-chloro-2-methoxypyridine (3.5 g, 24.38 mmol) in THF (8 mL) dropwise at -78 C. The reaction mixture turned into light yellow solution and was stirred at-78 C for 1 h, then DMF (3.78 mL, 48.8 mmol) was added dropwise. The reaction mixture was stirred at -78 C for lh. The reaction mixture was quenched with saturated NH4C1 solution at -78 C and the resulting mixture was stirred for 10 min and warmed up to rt. The resulting mixture was mixed with saturated NaHC03 solution and ethyl acetate. The organic layer was separated and washed with saturated NaHC03 solution, dried over MgS04. The filtrate was concentrated in vacuo. The residue was dissolved in DCM, purified via silica gel flash column chromatography, eluting with 0-25% ethyl acetate in hexane to give Intermediate 24A (white solid, 2.6 g, 15.15 mmol, 60% yield). LC-MS Anal. Calc’d for CvHeClNC 171.01, found [M+H] 172.1. Tr = 0.71 min (Method A). NMR (499MHz, chloroform-d) delta 10.47 (s, 1H), 8.20 (d, J=5.5 Hz, 1H), 7.01 (d, J=5.5 Hz, 1H), 4.08 (s, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72141-44-7, 4-Chloro-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; CHERNEY, Emily Charlotte; ZHANG, Liping; HUANG, Audris; SHAN, Weifang; WILLIAMS, David K.; ZHU, Xiao; GUO, Weiwei; (213 pag.)WO2018/209049; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 88312-64-5, 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 88312-64-5 as follows.

Preparation Example A+-9. 2-Amino-5-nitro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide 2-Amino-5-nitro-nicotinic acid methyl ester (48.4mg, 0.245mmol) described in Preparation Example A-3 and lithium hydroxide monohydrate (10.3mg, 0.245mmol) were dissolved in a solvent mixture of tetrahydrofuran (1mL), methanol (0.1mL) and water (0.1mL), and the solution was stirred for 17 hours at room temperature. The solvent was evaporated in vacuo, and 2-amino-5-nitro-nicotinic acid was obtained as a lithium salt. Then, the resulting lithium salt of 2-amino-5-nitro-nicotinic acid, C-(5-phenoxy-thiophen-2-yl)-methylamine (60mg, 0.29mmol), benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (162mg, 0.367mmol) and triethylamine (103mul, 0.735mmol) were dissolved in N,N-dimethylformamide (2.0mL), and the solution was stirred for 6 hours at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate, and the organic layer was washed with water and brine. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane : ethyl acetate = 1 : 1), and the title compound (87mg,0.24mmol,96%) was obtained as a pale yellow solid. 1H-NMR Spectrum (DMSO-d6) delta (ppm) : 4.49 (2H, d, J=5.5Hz), 6.50 (1 H, d, J=3.7Hz), 6.80 (1H, d, J=3.1Hz), 7.08 (2H, d, J=7.7Hz), 7.13 (1H, t, J=7.5Hz), 7.37 (2H, t, J=7.5Hz), 8.76 (1 H, d, J=2.2Hz), 8.96 (1 H, d, J=1.7Hz), 9.51 (1 H, t, J=5.5Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,88312-64-5, its application will become more common.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP1782811; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem