Tag: M.W:100-200

Reference of 115473-15-9, 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. 115473-15-9, name is 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride. A new synthetic method of this compound is introduced below.

Under nitrogen protection,A solution of 25.7 g (100 mmol) of 1-cyclopropyl-2-bromo-2- (2-fluorophenyl)2-oxo-2,4,5,6,7-7a-tetrahydrothieno [3,2-c] pyridine hydrochloride (28.7 g, 150 mmol)73 g (30 mmol) of cuprous iodide,Xphos 28.6 g (60 mmol), sodium carbonate 42.4 g (400 mmol) in 250 ml reaction flask, in 200 ml of 1,4-dioxane60 C for 3 hours. After the reaction, the mixture was cooled to room temperature, poured into ice water, extracted with methylene chloride, saturated sodium thiosulfateThe organic phase was concentrated and the mixture was recrystallized from dichloromethane and petroleum ether (1: 10) to give 5- (alpha-cyclopropylcarbonyl-2-fluorobenzyl)2-oxo-2,4,5,6,7,7a-tetrahydrothieno [3,2-c] pyridine in a yield of 90.2% and a purity of 99.37%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,115473-15-9, 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Qingdao Chenda Biological Science & Technology Co., Ltd.; Chen, Linghao; (8 pag.)CN106117240; (2016); A;,
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.73781-91-6, name is Methyl 6-chloronicotinate, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.Quality Control of Methyl 6-chloronicotinate

Reference example 56:; 2-Amino-N-(5-methoxycarbonyl-2-pyridyl)-2-methyl-amine [0263] To a solution of methyl 6-chloronicotinate (3.42 g, 20.0 mmol) in 2-propanol(20 mL) were added diisopropylethylamine (4.18 mL, 24.0 mmol) and 1,2-diamino-2-methylpropane (3.14 mL, 30.0 mmol), and the mixture was refluxed at 80 DEG C for 48 hours. The reaction mixture was concentrated under reduced pressure, and chloroform and aqueous potassium carbonate solution were added to the residue. The aqueous layer was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Chromatorex (registered trademark) NH, Fuji Silysia, hexane/ethyl acetate =5/1) to obtain the title compound (2.31 g, 10.3 mmol).yield: 52%<1>H NMR (CDCl3) delta (ppm): 8.71 (1H, d, J = 2.3 Hz), 7.95 (1H, dd, J = 8.9, 2.3 Hz), 6.40 (1H, d, J = 8.9 Hz), 5.53 (1H, t, J = 5.9 Hz), 3.86 (3H, s), 3.27 (2H, d, J = 5.9 Hz), 1.30 (2H, br s), 1.18 (6H, s).APCIMS (m/z): 224 (M + H)<+>

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73781-91-6, Methyl 6-chloronicotinate, and friends who are interested can also refer to it.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1354882; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 96530-81-3, 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 96530-81-3, name is 4-Fluoro-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

INTERMEDIATE 24 4-(3-Iodo-l H-pyrazol- 1 -yl)-2-methoxypyridine To 3-iodo-lH-pyrazole (763 mg, 3.93 mmol) in DMSO (15 mL) at 0 C, was added sodium hydride (60% in mineral oil, 189 mg, 4.72 mmol). The reaction was warmed to 25 C and stirred for 60 min before 4-fluoro-2-methoxypyridine (500 mg, 3.93 mmol) was added. The reaction mixture was stirred at 90 C for 4.5 h before quenching by the addition of water. The reaction mixture was extracted with EtOAc. The combined organic extracts were dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO Combiflash, 0-30% EtOAc in hexanes) to afford 4-(3-iodo-17J-pyrazol-l-yl)-2-methoxypyridine, as a white solid. LCMS calc. = 301.97; found = 302.02 (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 96530-81-3, 4-Fluoro-2-methoxypyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SMITH, Cameron, James; TAN, John, Qiang; ZHANG, Ting; BALKOVEC, James; GREENLEE, William, John; GUO, Liangqin; XU, Jiayi; CHEN, Yi-heng; CHEN, Yili; CHACKALAMANNIL, Samuel; HIRABAYASHI, Tomokazu; NAGASUE, Hiroshi; OGAWA, Kouki; WO2014/120346; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89937-77-9, Methyl 1,2-dihydro-2-oxopyridine-4-carboxylate, 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, 89937-77-9, blongs to pyridine-derivatives compound. COA of Formula: C7H7NO3

Step 1 4-Hydroxymethyl-1H-pyridin-2-one 2-Oxo-1,2-dihydropyridine-4-carboxylic acid methyl ester (1.8 g, 12.2 mmol), prepared as described in J. Org. Chem., 26, 428 (1961), was suspended in THF(100 ml). A small amount of DMF was added to help increase solubility. LiBH4 (61 mmol) was added and the reaction was stirred for 18 hours at room temperature. MeOH and H2 O are added to quench the reaction. The reaction is then concentrated to yield a yellow oil. Flash chromatography (5% MeOH/CHCl3 to 20% MeOH/CHCl3) yielded 4-hydroxymethyl-1H-pyridin-2-one as a white solid. 1 H NMR (400 MHz, CD3 OD) delta 7.38-7.36 (1H,d); 6.56 (s, 1H); 6.37-6.36 (d, 1H); 4.50 s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89937-77-9, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US6093737; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 34107-46-5 ,Some common heterocyclic compound, 34107-46-5, molecular formula is C7H9NO, 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.

Chromium trioxide (11.5 g) is slowly added to 170 ml of pyridine at 20C, and 10 g of the crude 5-hydroxy-methyl-2-methylpyridine in 70 ml of pyridine is added in one portion to the complex. The temperature is raised to reflux temperature for 2 hours, and the mixture is refluxed for 1.5 hours. After cooling, 250 ml of water is added, and the mixture is extracted with five 150-ml portions of diethyl ether. The combined extracts are dried over magnesium sulfate and concentrated to give 4.2 g of crude 6-methyl-3-pyridinecarbaldehyde.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,34107-46-5, its application will become more common.

Reference:
Patent; Dainippon Pharmaceutical Co., Ltd.; EP210782; (1991); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1628-89-3, 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. 1628-89-3, name is 2-Methoxypyridine, molecular formula is C6H7NO, 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.

General procedure: A stirred cooled (0 C) solution of LiTMP prepared at 0 C in THF (6 mL) from 2,2,6,6-tetramethylpiperidine (1.7 mL, 10 mmol) and BuLi (1.6 M hexanes solution, 10 mmol) was treated with TMEDA (0.77 mL, 5.0 mmol) and CuCl (495 mg, 5.0 mmol). The mixture was stirred for 15 min at 0 C before introduction of the required substrate (5 mmol). After 2 h at rt, a solution of the required aroyl chloride (10 mmol) in THF (3 mL) was added. The mixture was stirred at rt or 60 C overnight before addition of a 1 M aqueous solution of NaOH (20 mL) and extraction with Et2O (220 mL). After washing the organic phase with an aqueous saturated solutionof NH4Cl (10 mL) and drying over anhydrous Na2SO4, the solvent was evaporated under reduced pressure, and the product was isolated after purification by flash chromatography on silica gel (the eluent is given in the product description).

According to the analysis of related databases, 1628-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Marquise, Nada; Harford, Philip J.; Chevallier, Floris; Roisnel, Thierry; Dorcet, Vincent; Gagez, Anne-Laure; Sable, Sophie; Picot, Laurent; Thiery, Valerie; Wheatley, Andrew E.H.; Gros, Philippe C.; Mongin, Florence; Tetrahedron; vol. 69; 47; (2013); p. 10123 – 10133;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 10592-27-5, name is 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine

To a solution of sulfurisocyanatidic chloride (37 mg, 0.26 mmol) in DCM (2 mL) in an ice-water bath was added a solution of Intermediate GW-13.2 (100 mg, 0.26 mmol) and TEA (0.11 mL, 0.79 mmol) in DCM (2 mL) and the reaction mixture was stirred for 2 min. Then a solution of 2,3-dihydro-1H-pyrrolo[2,3-b]pyridine (48 mg, 0.39 mmol) in DCM (2 mL) was added, followed by TEA (0.15 mL, 1.1 mmol), the bath was removed and the stirring was continued at rt for 2 h. The reaction mixture was concentrated, the residue was redissolved in DMF and purified by preparative HPLC to afford the title compound (31.4 mg). LC-MS retention time = 3.06 min; m/z = 554.16 [M+Na]+. (Column: Phenomenex-Luna 2.0 X 50 mm, 3 mupiiota particles; Mobile Phase A: 10% MeOH- 90% H2O-0.1% TFA; Mobile Phase B: 90% MeOH-10% H2O-0.1% TFA; Temperature: 40 C; Gradient: 0-100% B over 4 min, then a 1-min hold at 100% B; Flow: 0.8 mL/min; Detection: UV at 220 nm).

With the rapid development of chemical substances, we look forward to future research findings about 10592-27-5.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BENDER, John A.; GENTLES, Robert G.; PENDRI, Annapurna; WANG, Alan Xiangdong; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; NGUYEN, Van N.; YANG, Zhong; WANG, Gan; KUMARAVEL, Selvakumar; THANGATHIRUPATHY, Srinivasan; BORA, Rajesh Onkardas; HOLEHATTI, Shilpa Maheshwarappa; METTU, Mallikarjuna Rao; PANDA, Manoranjan; (319 pag.)WO2016/172424; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 109-04-6, 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.109-04-6, name is 2-Bromopyridine, molecular formula is C5H4BrN, molecular weight is 157.996, as common compound, the synthetic route is as follows.

2-Bromopyridine (2.00 mL), 3-aminophenylboronic acid (5.40 g) and palladium tetrakistriphenylphosphine (1.2512 g) were added to a mixture of 130 mL of dimethoxyethane and 32 mL of 2.0 M aqueous potassium carbonate under an atmosphere of dry N2. The reaction mixture was heated at 90 C overnight. The reaction mixture was then cooled to room temperature and diluted with water (300 mL). The resulting precipitate was collected, washed with water and air-dried. The dried material was purified using silica gel chromatography to give 2.75 g of 3-(pyridin-2-yl)benzenamine.

Statistics shows that 109-04-6 is playing an increasingly important role. we look forward to future research findings about 2-Bromopyridine.

Reference:
Patent; ARRAY BIOPHARMA, INC.; WO2007/130743; (2007); A2;,
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. 100137-47-1, name is 4-Aminopicolinamide, molecular formula is C6H7N3O, 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. COA of Formula: C6H7N3O

To a solution of 4-aminopyridine-2-carboxamide (2.90 g, 21.2 mmol) and DIEA (7.19 g, 55.7 mmol) in NMP (27 mL) at 0 C was added dropwise a solution of 2-fluoro-4-(trifluoromethoxy)benzoyl chloride (5.40 g, 22.3 mmol) in dichloromethane (27 mL). The reaction mixture was removed from the ice bath and stirred at room temperature for 16 hours. The reaction mixture was partitioned between water and ethyl acetate. The layers were separated and the aqueous layer was extracted with additional ethyl acetate. The combined organic layers were dried over Na2S04, filtered and concentrated in vacuo. The crude material was triturated with a mixture of hexanes/dichloromethane and the solid was collected by vacuum filtration to obtain 4-[[2-fluoro-4-(trifluoromethoxy)benzoyl]amino]pyridine-2-carboxamide (650 mg, 9%). ESI-MS m/z calc. 343.05, found 344.1 (M+l)+; retention time (Method B): 1.65 minutes(3 minute run). NMR (400 MHz, DMSO-d6) delta 1 1.09 (s, 1H), 8.56 (d, J = 5.6 Hz, 1H), 8.36 (d, J = 2.2 Hz, 1H), 8.1 1 (d, J = 2.7 Hz, 1H), 7.95 – 7.80 (m, 2H), 7.74 – 7.54 (m, 2H), 7.50 – 7.32 (m, 1H) ppm.

With the rapid development of chemical substances, we look forward to future research findings about 100137-47-1.

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

Adding a certain compound to certain chemical reactions, such as: 16135-36-7, Methyl 4-aminonicotinate, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

A mixture of 4-chloro-5-isopropenyl-2 -phenyl-pyridine (1.2 g, 5.24 mmol), methyl 4- aminopyridine-3-carboxylate (795 mg, 5.225 mmol) and Cs2C03 (3.40 g, 10.435 mmol) in dioxane (30 mL) was purged with nitrogen for 30 min, followed by addition of Pd2(dba)3 (478 mg, 0.521 mmol) and xantphos (604 mg, 1.043 mmol) and again purged with nitrogen for 5 min. The reaction mixture was heated at 100 C overnight. The progress of reaction was monitored over LCMS. After completion of the reaction, the reaction mixture was diluted with water (100 mL) and extracted with EtOAc (2×150 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford a crude product, which was purified by column chromatography on silica gel (100-200 mesh) using 20% EtOAc- hexane as eluent to obtain methyl 4-[(5-isopropenyl-2-phenyl-4- pyridyl)amino]pyridine-3-carboxylate (500 mg) as a yellow sticky semi-solid

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16135-36-7, Methyl 4-aminonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; RAI, Roopa; CHAKRAVARTY, Sarvajit; PUJALA, Brahmam; SHINDE, Bharat Uttam; NAYAK, Anjan Kumar; CHAKLAN, Naveen; AGARWAL, Anil Kumar; RAMACHANDRAN, Sreekanth A.; PHAM, Son; WO2015/103355; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem