Tag: M.W:100-200

Application of 1945-84-2 ,Some common heterocyclic compound, 1945-84-2, molecular formula is C7H5N, 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.

General procedure: Catalyst (3 mol%) and phenylacetylene (0.5 mmol) were added to 2 mL DMSO solution. The mixture was stirred at 50 C under 1 atm pressure O2 for 6 h. The progress of the reaction was monitored by TLC. After completion of the reaction, 10 mL of ethyl acetate was added. The mixture was filtered through a pad of diatomite under reduced pressure, and the filtration residue was washed with ethyl acetate. Ethyl acetate was removed under reduced pressure. The residue was then purified by column chromatography on silica gel using petroleum ether as eluent to afford the corresponding 1,3-diynes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1945-84-2, its application will become more common.

Reference:
Article; Ma, Zongyan; Wang, Xiaoyu; Wei, Shuoyun; Yang, Honglei; Zhang, Fengwei; Wang, Peng; Xie, Miao; Ma, Jiantai; Catalysis Communications; vol. 39; (2013); p. 24 – 29;,
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.1824-81-3, name is 2-Amino-6-picoline, molecular formula is C6H8N2, molecular weight is 108.14, as common compound, the synthetic route is as follows.HPLC of Formula: C6H8N2

Step 1 Synthesis of 2,2-dimethyl-N-(6-methyl-2-pyridinyl)propaneamide (21-1) 2-amino-6-picoline (26 g) was dissolved in dichloromethane (280 ml) and the reactor was cooled to 0 C., followed by adding triethylamine (30. g) thereto. To the obtained solution was slowly added dropwise a solution of trimethylacetylchloride (31.8 g) in dichloromethane (20 ml) and the mixture was stirred at room temperature for 3 hours. The resulting mixture was filtered, washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure and then crystallized (dichloromethane/petroleum ether) to yield a pale yellow solid (38 g, 82%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1824-81-3, 2-Amino-6-picoline, and friends who are interested can also refer to it.

Reference:
Patent; Suh, Young Ger; Oh, Uh Taek; Kim, Hee Doo; Lee, Jee Woo; Park, Hyeung Geun; Park, Ok Hui; Lee, Yong Sil; Park, Young Ho; Joo, Yung Hyup; Choi, Jin Kyu; Lim, Kyung Min; Kim, Sun Young; Kim, Jin Kwan; Koh, Hyun Ju; Moh, Joo Hyun; Jeong, Yeon Su; Yi, Jung Bum; Oh, Young Im; US2003/153596; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1137-68-4, 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. 1137-68-4, name is 2-(2-Pyridyl)benzimidazole. A new synthetic method of this compound is introduced below.

Potassium hydroxide 51 mmol and 2-pyridylbenzimidazole were added to the reaction flask10.2 mmol, and 20 ml of 1-butyl-3-methylimidazolium hexafluorophosphate (ionic liquid) was added. After the mixture was stirred for 5 min in advance, 8 ml of 1,6-dibromohexane was added and the reaction was stirred for 5 h. After the reaction is complete, extract three times with ether, combine the oil phases, and use rotationThe evaporator removes the solvent. The resulting crude product was separated by column chromatography. The volume ratio of the eluent was petroleum ether:ethyl acetate=A 3:1 mixed solution finally gave 2.2 g of a colorless oily liquid with a yield of 60%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1137-68-4, 2-(2-Pyridyl)benzimidazole, and friends who are interested can also refer to it.

Reference:
Patent; Nanjing University of Posts and Telecommunications; Zhao Qiang; Yang Jiguang; Xu Wenjuan; Huang Wei; Liu Shujuan; Qin Yanyan; (26 pag.)CN106397488; (2017); A;,
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. 101012-32-2, name is (2-Chloropyridin-3-yl)acetonitrile. This compound has unique chemical properties. The synthetic route is as follows. Formula: C7H5ClN2

INTERMEDIATE 14 2-[(2-Fluoro-4-iodophenyl)amino1thieno[2,3-?]pyridme-3-carbonitrileTo a solution of (2-chloropyridin-3-yl)acetonitrile {Intermediate 2; 700 mg, 4.59 mmol) and Intermediate 4 (1.28 g, 4.60 mmol) in dry DMSO (15 mL) was added sodium hydride (202 mg, 60% in mineral oil, 5.06 mmol). The mixture was stirred at room temperature for 15 minutes before heating to 9O0C for four hours. The reaction mixture was poured into water (80 mL) and the solid precipitate filtered and washed with water/ ethanol (2:1 mixture, 50 mL) followed by diethyl ether/hexane (1:1 mixture, 20 mL). The solid was dried in a vacuum oven and recrystallised from ethanol/water to give the title compound as a pale brown solid (800 mg, 45%). ?H (DMSOd6) 10.40 (IH, s), 8.37 (IH, dd, J 1.3, 4.6 Hz), 7.83-7.81 (2H, m), 7.64 (IH, d, J 8.3 Hz), 7.44 (IH, dd, J 4.7, 8.0 Hz), 7.33 (IH, dd, J 8.3, 8.3 Hz). LCMS RT 3.08 minutes, (ES”) 394 (M-H)”, (ES+) 396 (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, 101012-32-2, (2-Chloropyridin-3-yl)acetonitrile.

Reference:
Patent; UCB PHARMA S.A.; WO2009/13462; (2009); 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. 118289-17-1, name is 2-Bromopyridine-4-carboxaldehyde. A new synthetic method of this compound is introduced below., Computed Properties of C6H4BrNO

To a stirred suspension of (R)-2-methylpropane-2-sulfinamide (13.03 g, 108 mmol) and CS2CO3 (52.5 g, 161 mmol) in DCM (400 ml) was added 2-bromopyridine-4- carbaldehyde (20 g, 108 mmol) over 10 min. The reaction mixture was then stirred for 18.5 h at rt. The reaction mixture was concentrated and the residue was diluted with EtOAc (50 ml) and washed with brine (3 x 20 ml). The organic layer was dried over MgS04 and filtered and then the filtrate was concentrated. The residue was purified by normal phase chromatography using hexanes and EtOAc as eluents to afford (27.2 g, 87%) of (R)-N-[(lE)-(2-bromopyridin-4-yl)methylidene]-2-methylpropane-2-sulfinamide as a white solid. MS(ESI) m/z: 289-291.0 (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, 118289-17-1, 2-Bromopyridine-4-carboxaldehyde.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DILGER, Andrew, K.; CORTE, James, R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; PABBISETTY, Kumar Balashanmuga; EWING, William, R.; ZHU, Yeheng; WEXLER, Ruth, R.; PINTO, Donald, J.P.; ORWAT, Michael, J.; SMITH II, Leon, M.; WO2015/116882; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 19621-92-2, 6-Oxo-1,6-dihydropyridine-2-carboxylic 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, Safety of 6-Oxo-1,6-dihydropyridine-2-carboxylic acid, blongs to pyridine-derivatives compound. Safety of 6-Oxo-1,6-dihydropyridine-2-carboxylic acid

At 25 C and N 2 atmosphere,To 6-hydroxypyridine-2-carboxylic acid (12 mmol)And pyridine (20 mmol)Add 20 mL of anhydrous dichloromethane solution1,3-Dicyclohexylcarbodiimide DCC (15 mmol).5 minutes later,Add 2-((1-Amino-2-methylpropan-2-yl)amino)-1-(5-hydroxy-1H-pyrrole[3,2]pyridin-1-yl)ethanone (10 mmol ),The mixture was stirred overnight.TLC (95:5 in dichloromethane:Methanol containing 2% ammonia)Indicates that all raw materials are consumed.The reaction was quenched with sodium bicarbonate and filtered through a pad of Celite.The stopper was rinsed with methylene chloride.The aqueous layer was extracted with dichloromethane.After the combined organic layers are dried over Na 2 SO 4 ,Filter and concentrate in vacuo,This gave 3.5 g of a light brown solid.The crude product was purified by flash chromatography.Use 2% to 8% MeOH:Purification by stepwise gradient of dichloromethane and 2% ammonia,Obtained 3.2 g of white powder as N-(2-((2-(5-hydroxy-1H-pyrrole[3,2]pyridin-1-yl)-2-ethoxy)amino)-2-methylpropane ()-(6-hydroxypyridin-2-yl)-carboxamide,The yield was 94%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,19621-92-2, 6-Oxo-1,6-dihydropyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Sang Qi; (10 pag.)CN108218865; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 878805-23-3, 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 878805-23-3 as follows.

Example 77 N-[(1S,2S)-2-Methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide A solution of (1S,2S)-1-methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine (Intermediate 25; 80 mg, 0.31 mmol), 3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxylic acid (CAS number 1252907-86-0; 70 mg, 0.37 mmol), EDC (177 mg, 0.92 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (126 mg, 0.922 mmol) and DIPEA (161 mul, 0.92 mmol) in dry DCM (1 ml) was stirred at room temperature overnight. The mixture was partitioned between ethyl acetate (20 ml) and water (10 ml). The organics were washed with water (2*10 ml), brine (10 ml), dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica, 0 to 100% ethyl acetate/petrol) followed by a trituration in pentane diethyl ether to afford the title compound. 1H NMR (400 MHz, DCM-d2) delta ppm 1.43 (s, 3H), 1.66-1.99 (m, 4H), 2.14-2.30 (m, 1H), 2.49-2.68 (m, 1H), 4.40-4.55 (m, 1H), 7.38-7.48 (m, 1H), 7.56 (br. s., 1H), 7.62-7.67 (m, 1H), 7.69 (br. s., 1H), 7.84 (s, 2H), 8.08-8.14 (m, 1H), 8.23 (br. s., 1H), 8.65-8.70 (m, 1H) MS ES+: 433 Example 89 3-Cyclopropyl-N-[(1S,2S)-2-methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]pyridine-2-carboxamide Prepared according to the procedure for N-[(1S,2S)-2-methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide (Example 77) from (1S,2S)-1-methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine (Intermediate 25; 48 mg, 0.15 mmol), 3-cyclopropylpyridine-2-carboxylic acid (Intermediate 16; 33 mg, 0.20 mmol) and triethylamine (0.077 ml, 0.55 mmol) except this was purified by column chromatography (silica, 0-50% ethyl acetate/petrol) followed by column chromatography (silica, 0-2.5% methanol/DCM) to afford the title compound. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 0.58-0.80 (m, 2H), 1.05-1.17 (m, 2H), 1.39 (s, 3H), 1.61-2.08 (m, 4H), 2.12-2.24 (m, 1H), 2.63 (s, 1H), 3.28-3.43 (m, 1H), 4.46-4.59 (m, 1H), 7.31-7.37 (m, 2H), 7.78-7.89 (m, 2H), 8.23-8.33 (m, 2H), 8.33-8.38 (m, 1H) MS ES1: 406

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,878805-23-3, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Fieldhouse, Charlotte; Glen, Angela; Maine, Stephanie; Fujimoto, Tatsuhiko; Robinson, John Stephen; US2015/232460; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 4548-45-2, 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.4548-45-2, name is 2-Chloro-5-nitropyridine, molecular formula is C5H3ClN2O2, molecular weight is 158.54, as common compound, the synthetic route is as follows.

Intermediate B-54-(5-Aminopyridin-2-yl)-N-(2-fluorophenyl)piperazine- 1 -carboxamide (B-5) Step 1 : t-Butyl 4-(5-nitropyridin-2-yl)piperazine-l-carboxylate (B-2)To 5-nitro-2-chloropyridine (10.0 g, 0.0631 raol) and N-BOC-piperazine (17.6 g, 0.0946 mol) dissolved in DMF (200 mL) was added N,N-diisopropylethylamine (24.5 g, 31.3 mL, 0.189 mol). The reaction mixture was heated at 100 C for 16 h then cooled to RT and concentrated. Water (300 mL) was added, and the aqueous solution was extracted with CH2G2. The combined organic extract was dried (MgS0 ), filtered, and concentrated.Purification by vacuum filtration through silica gel (eluant: 5% EtOAc-CFkCL.) gave t-butyl 4-(5-nitropyridin-2-yl)piperazine-l-carboxylate (B-2) as a yellow solid (19.45 g, 100% yield). MS (M+l): 309.

The chemical industry reduces the impact on the environment during synthesis 4548-45-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SCHERING CORPORATION; TING, Pauline, C.; LEE, Joe, F.; ASLANIAN, Robert, G.; WO2011/31628; (2011); 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.771579-27-2, name is 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one, molecular formula is C8H12N2O, molecular weight is 152.1937, as common compound, the synthetic route is as follows.Product Details of 771579-27-2

[0793] Step 4: Synthesis of 3-bromo-N-((4,6-dimethyl-2-oxo-l ,2-dihydropyridin-3- yl)methyl)-l-isopropyl-6-(4-(morpholinomethyl)phenyl)-lH-pyrazolo[3,4-b]pyridine-4- carboxamide[0794] A solution of 3-bromo-l-isopropyl-6-(4-(morpholinomethyl)phenyl)-lH- pyrazolo[3,4-b]pyridine-4-carboxylic acid (0.8 g, 1.74 mmol) and 3-(aminomethyl)-4,6- dimethylpyridin-2(lH)-one (0.53 lg, 3.49 mmol) in DMSO (8 raL) and was stirred at room temperature for 15 min. Then PYBOP (1.36 g, 2.62 mmol) was added to it and stirring was continued for 12 hr. After completion of the reaction, reaction mass was poured into ice to obtain solid, which was filtered and solid was purified by silica gel column cliromatography to obtain the desired compound (39% yield). LCMS: 593.20 (M + 1)+; HPLC: 97.49% (@ 254 nm) (R,;5.338); NMR (DMSO-i?, 400 MHz) delta 1 1.48 (bs, 1H), 8.67 (t, 1H, J=4.8 Hz), 8.18 (d, 2H, J= 8.4 Hz), 7.73 (s, 1H), 7.47 (d, 2H, .1=8.4 Hz), 5.87 (s, 1H), 5.33-5.30 (m, 1 H), 4.40 (d, 2H, J= 4.4 Hz), 3.58 (bs, 4H), 3.53 (s, 2H), 2.38 (bs, 4H), 2.26 (s, 3H), 2.1 1 (s, 3H), 1.52 (d, 6H, J=6.4 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,771579-27-2, 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; EPIZYME, INC.; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; CHESWORTH, Richard; DUNCAN, Kenneth, William; WO2012/118812; (2012); A2;,
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. 17282-00-7, name is 3-Bromo-5-methylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 3-Bromo-5-methylpyridin-2-amine

General procedure: Under N2 atmosphere, to a solution of palladium acetate (120 mg, 0.53 mmol, 5 mol %) and XANTPHOS (309 mg, 0.53 mmol, 5 mol %) in anisole (30 mL) was added 3-bromo-5-methyl-pyridin-2-ylamine (5) (2.0 g, 10.7 mmol, 1.0 equiv), aryl iodides (6) (10.7 mmol) and cesium carbonate (4.9 g, 15.0 mmol, 1.4 equiv), and the mixture was stirred at 130 C for 1-13 h. After cooling to room temperature, water (40 mL) was added to the mixture. The mixture was concentrated in vacuo and ethyl acetate (100 mL) was added to the residue. The organic layer was washed with water (20 mL) and concentrated in vacuo to give the crude product, which was purified by flash chromatography to give 7.

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, 17282-00-7, 3-Bromo-5-methylpyridin-2-amine.

Reference:
Article; Mineno, Masahiro; Sera, Misayo; Ueda, Tsuyoshi; Mizuno, Masahiro; Yamano, Mitsuhisa; Mizufune, Hideya; Zanka, Atsuhiko; Tetrahedron; vol. 70; 35; (2014); p. 5550 – 5557;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem