Month: April 2022

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.61310-37-0, name is 2-(Pyridin-2-yl)pyrimidin-4-amine, molecular formula is C9H8N4, molecular weight is 172.19, as common compound, the synthetic route is as follows.Safety of 2-(Pyridin-2-yl)pyrimidin-4-amine

General procedure: 1.1 eq of the appropriate acid and 1 eq of 25 was dissolved in 1 ml of HOBt solution in DMF (9.5percent wt). Then 1.2 eq of EDC was added and reaction mixture was left stirring at rt overnight (16-18h). After completion of the reaction, monitored by LCMS, the reaction mixture was diluted with 4 ml of distilled water and left at ultrasonic bath for 30-40 min. The resulting residue was filtered off, washed by water and dried under high vacuum to give the target compound. If there was no residue formed the aqueous solution was extracted by 4 ml of DCM and the organic layer was washed by water (2*4ml) and the solvent was removed under reduced pressure to give the target compound. In case of low purity of the final compound was subjected to preparative HPLC purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,61310-37-0, 2-(Pyridin-2-yl)pyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; SHY THERAPEUTICS LLC; HADARI, Yaron R.; CARTA, Luca; SCHMERTZLER, Michael; WILLIAMS, Theresa M.; REYNOLDS, Charles H.; HUTCHESON, Rebecca; (1452 pag.)WO2018/237084; (2018); A1;,
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. 4214-74-8, name is 3,5-Dichloropyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C5H4Cl2N2

K: 2-Amino-3,5-dichloropyridine J (10 g, 61.3 mmol) was dissolved in an aqueous HBr solution (100 mL 48% HBr, 200 niL H2O), then cooled to O0C. Br2 (10 mL) was added in one portion, followed by the dropwise addition OfNaNO2 solution (6.35 g, 92.0 mmol, 15 mL H2O). The mixture was stirred at O0C for 30 minutes, then allowed to warm to room temperature before being heated to 7O0C for 30 minutes. The cooled mixture was then neutralised with KOH solution (5.0 M) then extracted with ethyl acetate (3 x 200 mL), dried (MgSO4), filtered and concentrated. The residue was purified by chromatography (1:4 EtOAc, hexane) providing 8.2 g (59%) of K as a yellow crystalline solid. 1H NMR (300 MHz, CDCl3): delta 8.27 (d, J= 2.1 Hz, IH), 7.77 (d, J= 2.1 Hz, IH).

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, 4214-74-8, 3,5-Dichloropyridin-2-amine.

Reference:
Patent; BIONOMICS LIMITED; WO2008/70908; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 928653-73-0, 5-Bromo-2-chloro-3-iodopyridine, 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, SDS of cas: 928653-73-0, blongs to pyridine-derivatives compound. SDS of cas: 928653-73-0

To a reaction vessel (lO0mL) in a nitrogen environment containing 3 (5g, I 5.7mmol) were added trans-phenylvinylboronic acid 4 (2.7g, 1 8mmol), tetrakis triphenylphosphine (907mg, 0.8mmol), sodium carbonate (4.2g, 39mmol) in 1 ,4-dioxane(1 OOmL). The mixture was stirred at refiux for 24 hours until consumption of starting material followed by TLC. The product was cooled to room temperature; it was filtered on celite. The solution was dried on MgSO4, filtered and evaporated. The residue was purified by chromatography (c-hexane:ethyl acetate99: 1, then 98:2) to afford 5-bromo-2-chloro-3- ((E)-styryl)pyridine 5 (yield: 93%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,928653-73-0, 5-Bromo-2-chloro-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; CENTRE REGIONAL DE LUTTE CONTRE LE CANCER FRANCOIS BACLESSE; UNIVERSITE DE CAEN BASSE-NORMANDIE; INSTITUT DE CANCEROLOGIE DE L’OUEST RENE GAUDUCHEAU; POULAIN, Laurent; VOISIN-CHIRET, Anne-Sophie; SOPKOVA-DE OLIVEIRA SANTOS, Jana; BUREAU, Ronan; BURZICKI, Gregory; DE GIORGI, Marcella; PERATO, Serge; FOGHA, Jade; RAULT, Sylvain; JUIN, Philippe; GAUTIER, Fabien; WO2015/132727; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1133879-69-2, 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 1133879-69-2, name is 3-Fluoro-5-vinylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of tetrahydrocarbazole 5a (0.17 g,1 mmol), 5fluoro3vinylpyridine (6) (0.12 g, 1 mmol), CsF(0.1 g), and hydroquinone (0.02 g) in DMSO (1.5 mL) was heated with stirring at 130-140 C for 4 h, DMSO was evaporatedin vacuo (3 Torr), the product was extracted from residue withdichloromethane. The solvent was evaporated and the residuewas subjected to chromatography on silica gel (60 mesh), eluentmethanol-chloroform = 1 : 5. The yield was 0.22 g (75%), m.p.65-67 C. Found (%): C, 77.63; H, 6.43; N, 9.64. C19H19FN2.Calculated (%): C, 77.52; H, 6.45; N, 9.52. 1H NMR (DMSOd6), : 1.81 (m, 4 H, CH2); 2.29 (m, 2 H, CH2); 2.72 (m, 2 H,CH2); 3.05 (t, 2 H, CH2Py, J = 6.8 Hz); 4.25 (t, 2 H, CH2N,J = 6.9 Hz); 6.80 (dt, 1 H, CHPy, JHF = 9.3 Hz, JHH = 2.4 Hz);7.05-7.30 (m, 3 H, CHAr); 7.50 (d, 1 H, CHAr, J = 6.8 Hz); 8.14(s, 1 H, CHPy); 8.34 (d, 1 H, CHPy, JHH = 2.4 Hz). 19F NMR(DMSOd6), : -49.38 (d, JFH = 9.4 Hz).

According to the analysis of related databases, 1133879-69-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sokolov; Aksinenko; Nikolaeva; Grigor’Ev; Kinzirsky; Bachurin; Russian Chemical Bulletin; vol. 63; 5; (2014); p. 1137 – 1141; Izv. Akad. Nauk, Ser. Khim.; 5; (2014); p. 1137 – 1141,5;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 100202-78-6, 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 100202-78-6 as follows.

EXAMPLE 14 SYNTHESIS OF (2-DIMETHYLAMINO-3,5,6-TRIFLUOROPYRIDIN-4-YL)METHYL CIS-3-(2-CHLORO-3,3,3-TRIFLUOROPROPENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE By the method of Example 2, 0.5 g (0.002 mole) of 2-dimethylamino-4-hydroxymethyl-3,5,6-trifluoropyridine (from Example 13) was reacted with 0.6 g (0.002 mole) of cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarbonyl chloride to produce, after purification through a short silica gel column and the Chromatotron, 0.45 g of (2-methoxy-3,5,6-trifluoropyridin-4-yl)methyl cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate as an oil, Compound No. 20 of the tables below. Analysis calc’d for C17 H17 ClF6 N2 O2: C 47.38; H 3.95; N 6.50; Found: C 47.69; H 4.09; N. 6.55.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,100202-78-6, its application will become more common.

Reference:
Patent; FMC Corporation; US4701464; (1987); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 83664-33-9, 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.83664-33-9, name is 2-(Benzyloxy)-5-bromopyridine, molecular formula is C12H10BrNO, molecular weight is 264.12, as common compound, the synthetic route is as follows.

Manufacturing Example 12-1-2 6-Benzyloxy-pyridin-3-carbaldehyde; To a solution of 2-benzyloxy-5-bromopyridine (15.1 g, 57.0 mmol) described in Manufacturing Example 12-1-1 in anhydrous tetrahydrofuran (250 mL) were added dropwise n-butyl lithium (2.67 M n-hexane solution, 25.6 mL, 68.4 mmol) under nitrogen atmosphere on a dry ice-ethanol bath (-78 C.), which was stirred for 30 minutes at -78 C. N,N-Dimethylformamide (6.60 mL, 85.5 mmol) was then added thereto at -78 C, and stirred for 30 minutes. Water and ethyl acetate were added to the reaction mixture, and the organic layer was separated after stirring for 10 minutes at room temperature. The organic layer was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate_heptane=1:7 then 1:5) to obtain the title compound (4.87 g, 40%).1H-NMR Spectrum (CDCl3) delta (ppm): 5.49 (2H, s), 6.89-6.92 (1H, m), 7.34-7.48 (5H, m), 8.07-8.10 (1H, m), 8.64-8.65 (1H, m), 9.97 (1H, s).

The chemical industry reduces the impact on the environment during synthesis 83664-33-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Tanaka, Keigo; Yamamoto, Eiichi; Watanabe, Naoaki; US2009/82403; (2009); A1;,
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. 914942-88-4, name is tert-Butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C13H18IN5O2

A1.12 (1.48 g, 3.66 mmol), dichlorobis(triphenylphosphine)palladium (155 mg, 0.22 mmol), 3-ethynylbenzonitrile (A2.2) (930 mg, 7.32 mmol) and triethylamine (12 mL) were added to N,N-dimethylformamide (8 mL). The reaction mixture was heated at 90 0C for 50 min, cooled and the solvent removed under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate as the eluent to provide 960mg (65%) of A2.3. M+H+ = 403.21. Alternate preparation:A1.12 (8.0 g, 19.85 mmol), dichlorobis(trirhohenylphosphine)palladium (840 mg, 1.2 mmol), 3-ethynylbenzonitrile (A2.2) (3.2g, 25.0 mmol) and triethylamine (60 mL) were each added to N,N-dimethylformamide (40 mL), and nitrogen was bubbled through the resulting mixture for 5min. The reaction mixture was heated at 90 0C for 20 min under a nitrogen atmosphere before cooling to room temperature and evaporating the solvent in vacuo. The residue was purified by silica gel column chromatography using ethyl acetate as eluent to provide 6.5g (81%) of A2.3 HPLC YMC S-5 4.6x33mm (2min grad): retention time 2.80min, M+H4″ = 403.21

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, 914942-88-4, tert-Butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 947249-13-0, 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. 947249-13-0, name is 5-Bromo-3-(difluoromethoxy)pyridin-2-amine, molecular formula is C6H5BrF2N2O, 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.

Step 4:84To a solution of compound 83 ( 5.61 g, 23.5 mmol) in acetonitrile (250 mL) was added di-terf- butyl-dicarbonate (15.65 g, 71.71 mmol), 4-(dimethylamino)pyridine (571 mg, 4.67 mmol), and triethyl amine (16.5 mL, 118 mmol). The mixture was stirred at room temperature for 1.5 hours, then concentrated to dryness and purified by silica gel chromatography (eluting with 10-25% ethyl acetate in hexanes gradient) to give compound 84 (9.53 g, 92.4%) as a white solid.

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 947249-13-0, 5-Bromo-3-(difluoromethoxy)pyridin-2-amine.

Reference:
Patent; PFIZER INC.; WO2009/16460; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 138588-22-4, 3-(Pyridin-2-yl)-1,2,4-thiadiazol-5-amine, 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, 138588-22-4, blongs to pyridine-derivatives compound. Formula: C7H6N4S

3-Pyridm-2-yl-[l,2,4]thiadiazol-5-yIamine (50 mg, 0.28 mmol) and p-chlorobenzoic acid (44 mg, 0.28 mmol) were mixed in 1 mL of anhydrous dimethvlformamide, to which solution was added N,N-diisopropylethylamine (0.1 mL, 0.58 mmol) followed by addition of 1 – [his(dimethylammo)methylene]~ 1H- 1 ,2,3-triazolo[4,5-b]pyridinium 3 -oxide hexafluorophosphate (1 14 mg, 0.30 mmol). The mixture was stirred under nitrogen at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography to obtain Compound 7 as a white solid (53.5 mg, 60%). NMR (400 MHz, DMSO-rfe) delta ppm 7.36 – 7.64 (m, 1 H) 7.69 (d, J=8.69 Hz, 2 H) 7.91 – 8.10 (m, 1 H) 8.12 – 8.34 (m, 3 H) 8.72 (d, J=4.00 Hz, 1 H); LCMS (M/Z): M+HT’ 317.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,138588-22-4, its application will become more common.

Reference:
Patent; SCYNEXIS INC.; LIU, Hao; SLIGAR, Jessica, Marie; SPEAKE, Jason, Daniel; MOORE, Joseph, A., III; BECK, Brent, Christopher; WO2015/73797; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 98273-79-1, Methyl 3-chloroisonicotinate, 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, COA of Formula: C7H6ClNO2, blongs to pyridine-derivatives compound. COA of Formula: C7H6ClNO2

To a solution of 3-chloro-pyridine-4-carboxylic acid methyl ester (0.28 g, 1.65 mmol) in DMF (10 ml) are added cesium carbonate (2.68 g, 8.25 mmol) and 3,3-difluoro-3-(4-fluorophenyl)-propane-1-thiol (synthesized according to the methods described in sections a) and b) of example 3) (0.34 g, 1.65 mmol) in a sealed tube. The reaction mixture is stirred at 90 C. for 1 h. After completion of the reaction, the mixture is diluted with water (15 ml) and extracted with EtOAc (3×20 ml). The organic layer is washed with water (20 ml), brine (20 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 10% acetone/hexane) to yieldb3-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-pyridine-4-carboxylic acid methyl ester (0.19 g, 0.56 mmol, 34%).

The synthetic route of 98273-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; LUCAS, Simon; Kuehnert, Sven; Bahrenberg, Gregor; Schroeder, Wolfgang; US2014/148468; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem