Month: April 2022

Electric Literature of 1027785-19-8, 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 1027785-19-8 as follows.

B) To a suspension of compound A of Example 5 (1.9 g, 9.36 mmol) in toluene (20 mL) was added activated Mntheta2 (2.2 g, 25.6 mmol) and the mixture was heated to 80 0C with vigorous stirring. After 2 h, the mixture was cooled to RT and filtered. The filtrate was concentrated in vacuo to obtain 6-amino-5- bromonicotinaldehyde as a solid (1.8 g, 96%). LC/MS; (M+H)+ = 203, 201 (1: 1 ratio). 1H NMR (CD3OD, 300 MHz) delta 9.59 (s, IH), 8.34 (s, IH), 8.03 (s, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1027785-19-8, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/60907; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 98353-08-3, 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. 98353-08-3, name is 5-Ethoxypicolinic acid. A new synthetic method of this compound is introduced below.

5-Ethoxypicolinic acid (53.6 mg, 320 muiotaetaomicron) was suspended in dichloromethane (5 mL), the suspension was cooled to 0-5C (ice bath) and oxalyl chloride (56.9 mg, 39.3 mu, 448 muiotaetaomicron) as well as dimethylformamide (0.308 M in toluene, 51.9 mu, 16 muiotaetaomicron) were added. The mixture was stirred for 2.5 h at room temperature. Then, it was concentrated in vacuo (40C, 5 mbar) and dried azeotropically by two cycles of addition of toluene (3 mL) followed by concentration in vacuo to afford 5-ethoxypicolinoyl chloride as purple oil (59 mg, quant.). After that, tert-butyl ((3aS,4R,8R)-4-(5-amino-2-fluorophenyl)-4,7,7-trimethyl-8-oxido-3,3a,4,7-tetrahydro-2H- isothiazolo[l,5-a][l,4]thiazin-6-yl)carbamate (Int-16ABp, 80 mg, 188 muiotaetaomicron) was dissolved in dichloromethane (5 mL), the solution cooled to 10C and N,N-diisopropylethylamine (36.5 mg, 49.4 mu, 283 muiotaetaomicron) was added, followed by a solution of 5-ethoxypicolinoyl chloride (vide supra, 47.5 mg, 256 muiotaetaomicron) in dichloromethane (4 mL). The reaction mixture was stirred for 15 min at 10C. Then, methanol (2 mL) was added, the mixture was stirred for 5 min at room temperature and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 24 g, eluting with 2 M ammonia in methanol / dichloromethane, gradient 1:99 to 3:97) to yield, after drying in vacuo (40C, 5 mbar), the title compound as a colorless viscous oil (95 mg, 88% yield). HPLC (method LCMS_fglm) tR = 1.36 min. MS (ES+) m/z 574.4 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98353-08-3, 5-Ethoxypicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; OBST SANDER, Ulrike; VIFIAN, Walter; WOLTERING, Thomas; (89 pag.)WO2017/25491; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 89466-17-1, Adding some certain compound to certain chemical reactions, such as: 89466-17-1, name is 6-Bromo-5-methylpyridin-2-amine,molecular formula is C6H7BrN2, 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 89466-17-1.

To a stirred solution of (2S,4R)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (250 mg, 1.07 mmole) in 10 mL of CH2Cl2, was added 1-methyl imidazole (0.21 mL, 2.5 equiv.) at 0-5 C. under nitrogen atmosphere. The reaction mixture was stirred for 10 min at 0-5 C. and then added methane sulfonyl chloride (0.1 mL, 1.2 equiv) at the same temperature. It was stirred for 1 h at 0-5 C. Then 6-bromo-5-methylpyridin-2-amine (200 mg, 1 equiv) was added, and stirred for 18h at room temperature. Water (10 mL) was added to the reaction mixture, layers were separated and aqueous layer was extracted with DCM (3×10 mL). The combined organic layer was washed with 1N HCl (10 mL), followed by Sat NaHCO3 (10 mL) and then with brine (10 mL). Combined organic layer was dried over Na2SO4, concentrated and to obtain titled compound 404 mg (quantitative yield).

According to the analysis of related databases, 89466-17-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); 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. 2897-43-0, name is 2,6-Dichloro-3-nitropyridin-4-amine. A new synthetic method of this compound is introduced below., Application In Synthesis of 2,6-Dichloro-3-nitropyridin-4-amine

6-Chloro-3-nitro-N2-(quinolin-6-ylmethyl)pyridine-2,4-diamine To a mixture of 2,6-dichloro-3-nitropyridin-4-amine (624 mg, 3 mmol) and quinolin-6-ylmethanamine (316 mg, 2 mmol) in CH3CN (10 mL) was added Et3N (0.5 mL). The reaction mixture was stirred at 80 C. for 1 h. After cooled to room temperature, the mixture was concentrated to afford the title compound (658 mg). MS (m/z): 330 (M+1)+.

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, 2897-43-0, 2,6-Dichloro-3-nitropyridin-4-amine.

Reference:
Patent; SU, Wei-Guo; JIA, Hong; DAI, Guangxiu; US2012/245178; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 60753-14-2, 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.60753-14-2, name is 4-(Pyridin-3-yl)butan-1-ol, molecular formula is C9H13NO, molecular weight is 151.21, as common compound, the synthetic route is as follows.

EXAMPLE 122 Preparation of alpha-oxo-4-[4-(3-pyridinyl)butoxy]benzeneacetic acid methyl ester (4:1) molar hydrate A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (1.14 g), 3-pyridinebutanol (1.04 g), triphenylphosphine (2.07 g), and tetrahydrofuran (25 mL) was stirred at 0 C. while adding dropwise a solution of diethyl azodicarboxylate (1.37 g) in tetrahydrofuran (10 mL). The mixture was stirred for 2 hours at 0 C. and evaporated to dryness. The material was purified by HPLC (hexane-acetone; 2:1) to provide 1.4 g of alpha-oxo-4-[4-(3-pyridinyl)butoxy]benzeneacetic acid methyl ester (4:1) molar hydrate as a colorless oil. Analysis Calculated for C18 H19 NO4.4:1H2 O: C, 68.02; H, 6.18; N, 4.41. Found: C, 68.24; H, 6.19; N, 4.68.

The chemical industry reduces the impact on the environment during synthesis 60753-14-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hoffman-La Roche Inc.; US5344843; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1149-24-2, Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, 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, Computed Properties of C13H17NO4, blongs to pyridine-derivatives compound. Computed Properties of C13H17NO4

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1149-24-2, Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 75073-11-9, 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.75073-11-9, name is 5-Iodo-6-methylpyridin-2-amine, molecular formula is C6H7IN2, molecular weight is 234.04, as common compound, the synthetic route is as follows.

(B) 6-iodo-5-methylimidazo[1,2-a]pyridine (0308) To a solution of 5-iodo-6-methylpyridin-2-amine (7.5 g, 32 mmol) in ethanol (400 mL) was added 2-chloroacetaldehyde aqueous solution (18 mL, 40%), and the mixture was stirred at 80 C for 16 hr. After cooling, the reaction mixture was concentrated under reduced pressure, and the residue was diluted with water, neutralized with 30% aqueous sodium hydroxide solution, and extracted with dichloromethane (150 mL×3). The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained solid was washed with ethyl acetate to give the title compound (6.0 g). MS: [M+H]+ 259.1

Statistics shows that 75073-11-9 is playing an increasingly important role. we look forward to future research findings about 5-Iodo-6-methylpyridin-2-amine.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KIMURA, Eiji; MIYANOHANA, Yuhei; OGINO, Masaki; TANAKA, Yuta; FUSHIMI, Makoto; OKAWA, Tomohiro; HANYA, Yuki; KOIKE, Tatsuki; (67 pag.)EP3239150; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 53636-70-7, 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 53636-70-7, name is 6-Methyl-2,3-pyridinedicarboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLES Example 1 N-(2-Amino-6-methylpyridin-3-ylmethel .-N- {2-[2-[(2-amino-6-methyl-pyndin-3- ylmethyl fbrmylammo]-l- (2-hydroxyethyl)-propenyldisulfanyl]-4-hydroxy-l- methylbut-1-enyl} formamide (III-13) [0115] a) 2-Methylfuro[3,4-b]pyridine-5,7-dione. To a solution of 6-methyl-2,3- pyridinedicarboxylic acid (41*5g, 229mmol) and acetic anhydride (70mL) in 250mL of 1,2-dimethoxyethane was added pyridine (37mL). The reaction mixture was stirred at room temperature for 90 min. The solution was diluted with ether (50mL) and hexane (150mL) was added until the solution became cloudy. The solution was stirred in an ice-water bath until a white precipitate formed. The precipitated solid was collected by filtration and dried under vacuum overnight to give 20.7g (55%) of the title compound as a white crystalline solid. 1H NMR (CDCl3) 8 2. 85 (s, 3H), 7. 68 (d, 1H), 8.25 (d, 1H).

According to the analysis of related databases, 53636-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA INC.; WO2005/95344; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 72716-80-4 ,Some common heterocyclic compound, 72716-80-4, molecular formula is C8H8N2O, 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 suspension of 3-cyano-5,6-dimethyl-2-pyridone (1-013-02) (12.0 g) in water (293 mL) was added conc. hydrochloric acid (293 mL), and the reaction mixture was reflux with stirring in oil-bath at 135 DEG C. After 3 days, the reaction mixture was cooled, and evaporated under reduced pressure. To the residue (24.75 g) were added chloroform (300 mL) and methanol (15 mL), and the reaction mixture was heated in a water bath at 65 DEG C, and the dissolble material was filtered off. Furthermore, the dissolble material was treated by chloroform (200 mL) and methanol (10 mL) in a similar manner to described above. The combined filtrates were evaporated under reduced pressure. To the obtained residue (13.26 g) were added methanol (150 mL) and potassium carbonate (10 g). After stirred at room temperature for 30 min, the dissolble material was filtered off. The filtrate was evaporated under reduced pressure. To the obtained residue (14.7 g) was added chloroform (200 mL), and the dissolble material was filtered off again. The filtrate was evaporated under reduced pressure to give 5,6-dimethyl-2-pyridone (1-013-03) (9.41 g, 94.3%, m.p.: 202-207 DEG C)<1>H NMR (300 MHz, CDCl3): delta 2.05 (s, 3H), 2.31 (s, 3H), 6.38 (d, J = 9.0 Hz, 1H), 7.26 (d, J = 9.0 Hz, 1H), 13.17 (br 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,72716-80-4, its application will become more common.

Reference:
Patent; SHIONOGI & CO., LTD.; EP1357111; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 109306-86-7 ,Some common heterocyclic compound, 109306-86-7, molecular formula is C11H8BrN, 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.

(a) 2-[2-(2-Pyridyl)-phenyl thio]-benzoxazole 2-Mercapto benzoxazole (604 mg; 4 mmole) was reacted with 2-(2-bromophenyl)pyridine (936 mg; 4 mmole) in the presence of KOH (224 mg; 4 mmole) in N-methyl pyrrolidine (16 ml). The mixture was heated under reflux for 6 hours, worked up and flash chromatographed (silica), using ethyl acetate/petroleum ether (2/3) eluant to give the sub-title compound as a pale brown oil (52 mg; 4.3%). m/z 304, 281, 277, 271, 186 (Base Peak), 154, 135.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,109306-86-7, its application will become more common.

Reference:
Patent; Fisons plc; US4900751; (1990); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem