Tag: M.W:100-200

Synthetic Route of 918511-92-9, 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. 918511-92-9, name is 5-(Pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine, molecular formula is C12H9N3, 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 3-nitrobenzaldehyde (534, 1.08 g, 7.17 mmol) in methanol (34 niL) was added 5- pyridin-3-yl-lH-pyrrolo[2,3-b]pyridme (89, 1.08 g, 5.52 mmol, prepared as described in Example 17) and potassium hydroxide (1.55 g, 27.6 mmol). The reaction was stirred at room temperature for four hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The mixture was purified by silica gel column chromatography eluting with 4% methanol in dichloromethane to provide two different compounds, a white solid (P-1399, R = H, 1.20 g, 63%) MS(ESI) [MMf]+ = 347.2, and a light yellow solid (535, R = Me, 0.434 g, 22%).

According to the analysis of related databases, 918511-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PLEXXIKON, INC.; WO2007/2325; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58530-50-0, 2-(Pyridin-2-yloxy)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, 58530-50-0, blongs to pyridine-derivatives compound. Quality Control of 2-(Pyridin-2-yloxy)acetic acid

General procedure: To the mixture of compounds (IVa-c)(2 mmol) in dry acetonitrile (15 mL), triethylamine(3 mmol) followed by substituted piperazines(2 mmol) was added. The mixture was stirred for30 min and TBTU (2mmol) was then added and stirring was continued at room temperature under an inert atmosphere for 10-24 h; the completion of thereaction was monitored by TLC using chloroform-methanol (9 : 1) as eluent. The solvent was evaporatedat reduced pressure, quenched by the addition of coldwater (20 mL), and the obtained solids (Va), (Vb), (Vc),(Vd), (Ve), (Vf), (Vi), and (Vk) were filtered, dried, andrecrystallized from ethanol. In contrast, compounds(Vg), (Vh), (Vj), and (Vl) were obtained by extractingwith ethyl acetate. The extract was washed successivelywith a solution of 10% HCl (20 mL), 10% NaHCO3(20 mL), and water (20 mL). The organic layer wasdried over anhydrous sodium sulfate and evaporated,the crude product was purified by column chromatography (eluent: hexane-dichloromethane-acetone,5 : 3 : 2) to achieve pure piperazine derivatives. Thephysical and analytical data of the synthesized titlecompounds (Va-l) are given below.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58530-50-0, its application will become more common.

Reference:
Article; Al-Ghorbani; Rekha; Lakshmi Ranganatha; Prashanth; Veerabasappagowda; Khanum; Russian Journal of Bioorganic Chemistry; vol. 41; 5; (2015); p. 554 – 561; Bioorg. Khim.; vol. 41; 5; (2015); p. 554 – 561,8;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73027-79-9, 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 73027-79-9, name is 4,6-Dichloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 4,6-dichloronicotinic acid (1 .0 g, 5.21 mmol) in N,N-dimethylformamide (15 mL) was added N,O-dimethylhydroxylamine (1 .02 g, 10.42 mmol), hydroxybenzotriazole (1 .41 g, 10.4mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (2.0 g, 10.4 mmol) and N-ethyl-N-(propan-2- yl)propan-2-amine (2.02 g, 15.6 mmol, 2.73 mL). The mixture was stirred at 20 00 for 48 h. The reaction mixture was quenched by addition of water (20 mL) then the mixture was extracted with ethyl acetate (50 mL x 3). The combined organic phases were washed with saturated aqueous sodium chloride solution (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give a crude residue that waspurified by chromatography (silica, petroleum ether : ethyl acetate 50:1 to 5:1 to give 4,6-dichloro-N- methoxy-N-methylnicotinamide (660 mg, 2.81 mmol, 54 %) as a yellow oil.1H NMR (400 MHz, ODd3) O 8.37 (s, 1 H), 7.45 (s, 1 H), 3.51 (br s, 3H), 3.40 (br s, 3H).

According to the analysis of related databases, 73027-79-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; YUMANITY THERAPEUTICS; LUCAS, Matthew; LE BOURDONNEC, Bertrand; WRONA, Iwona; PANDYA, Bhaumik; TIVITMAHAISOON, Parcharee; OZBOYA, Kerem; VINCENT, Benjamin; TARDIFF, Daniel; PIOTROWSKI, Jeff; SOLIS, Eric; SCANNEVIN, Robert; CHUNG, Chee-Yeun; ARON, Rebecca; RHODES, Kenneth; (489 pag.)WO2018/81167; (2018); A1;,
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 1721-26-2, name is Ethyl 2-methylnicotinate. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C9H11NO2

EXAMPLE 181 3-{[5-(2-Adamantan-1-yl-ethyl)-2-(2-methyl-pyridine-3-yl)-1H-imidazole-4-carbonyl]-amino}-benzoic Acid 5-(2-Adamantan-1-yl-ethyl)-2-(2-methyl-pyridine-3-yl)-1H-imidazole-4-carboxylic acid was prepared according to the procedure of Example 70, steps a and b, with the modification that 2-methyl-pyridine-3-carboxaldehyde (prepared from ethyl 2-methylnicotinate in two steps) was used in step a instead of 2-dimethylamino-benzaldehyde. It was reacted with 3-amino-benzoic acid benzyl ester according to the procedure of Example 20, step d to afford 3-{[5-(2-adamantan-1-yl-ethyl)-2-(2-methyl-pyridine-3-yl)-1H-imidazole-4-carbonyl]-amino}-benzoic acid benzyl ester. The benzyl group was removed following the procedure of Example 1, step e, to afford the title compound as a white solid. 1H NMR (300 MHz, d6-DMSO) 12.70 (1H, br s), 9.77 (1H, s), 8.49 (2H, m), 7.97 (2H, m), 7.62 (1H, d), 7.41 (1H, t), 7.35 (1H, dd), 2.87 (2H, m), 2.76 (3H, s), 1.95 (3H, br s), 1.69 (6H, m), 1.54 (6H, m), 1.44 (2H, m).

With the rapid development of chemical substances, we look forward to future research findings about 1721-26-2.

Reference:
Patent; James Black Foundation Limited; US6479531; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 527681-61-4, name is 3,4-Dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde, the common compound, a new synthetic route is introduced below. HPLC of Formula: C9H9NO2

suspension of (1 /?)-1-[(4-amino-1-piperidinyl)methyl]-6-methyl-1 ,2-dihydro- 4H,9H-imidazo[1 ,2,3-ij]-1 ,8-naphthyridine-4,9-dione dihydrochloride (50mg, 0.135 mmol) in chloroform (4 ml) and methanol (0.200 ml) at room temperature under nitrogen was treated with triethylamine (0.057 ml, 0.406 mmol) and stirred for 0.25h (the suspension turned into a solution). 3,4-Dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde (for a synthesis see WO2004058144, example 5(c)) (22.06 mg, 0.135 mmol) was then added and the reaction was stirred at room temperature for 0.5h.Sodium triacetoxyborohydride (90 mg, 0.406 mmol) was then added and the reaction was stirred at room temperature. After 2h there was still some starting material so 30 mg of sodium triacetoxyborohydride were added. After 1 h sat NaHCO3 (25ml_) was added followed by 20% MeOH/DCM (25ml_) and the aqueous was extracted and then separated from the organic layer. The aqueous was extracted again twice with 20%MeOH/DCM (2x25ml_). Combined organics were dried NaSO4, filtered and evaporated to afford the crude. The crude was purified by silica chromatography (0- 20%MeOH/DCM) to afford 41 mg of desired compound (65.7%) as a pale yellow gum. 1H NMR deltaH CDCI3, (400MHz) 1.30-1.45 (m, 2H), 1.80-1.89 (m, 2H), 1.99-2.05 (m, 2H), 2.15-2.4 (m, 5H), 2.45-2.58 (m, 1 H), 2.62-2.67 (m, 2H), 2.74-2.78 (m, 2H), 2.96 (d, 1 H), 3.05-3.09 (m, 1 H), 3.79 (s, 2H), 4.19-4.22 (m, 2H), 4.28-4.33 (m, 1 H), 4.51-4.55 (m, 1 H), 4.95-5.05 (m, 1 H), 6.15 (s, 1 H), 6.26 (d, 1 H), 6.97 (s, 1 H), 7.56 (d, 1 H), 8.07 (s, 1 H). MS (ES+) m/z 462 (MH+).The compound was dissolved in a small amount of MeOH/DCM and treated with 1eq of a 1 M solution of HCI in diethyl ether. The solvents were removed and the solid was dried in the desiccator (in the presence of P2O5) overnight to afford the mono-HCI salt of the product as a yellow solid (45.9mg, 64.8%). LCMS was consistent with product

The synthetic route of 527681-61-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; GIORDANO, Ilaria; HENNESSY, Alan, Joseph; WO2010/43714; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 122307-41-9 , The common heterocyclic compound, 122307-41-9, name is 4-Chloro-3-methoxy-2-methylpyridine 1-oxide, molecular formula is C7H8ClNO2, 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.

b 2-Methyl-3-methoxy-4-(2,2,2-trifluoroethoxy)pyridine N-oxide 6.7 g of potassium tert-butoxide were added in portions, at -20 C., while stirring and under a nitrogen atmosphere, 5 to 20 ml of trifluoroethanol. After the mixture had been warmed to 0 C., 5.2 g (30 mmol) of 2-methyl-3-methoxy-4-chloropyridine N-oxide were added in portions. The mixture was heated under reflux for 3 hours, and then left to cool down to room temperature; a further 3.45 g of potassium tert-butoxide were then added and the mixture was heated under reflux for 2 hours. After it had cooled down, 40 ml of water were added to the reaction mixture, which was then extracted with dichloromethane; the extract was then dried over MgSO4 and freed from the solvent in vacuo. The resulting oily product was subjected to further reaction.

The synthetic route of 122307-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoechst Aktiengesellschaft; US5658933; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 10201-73-7, name is 2-Amino-4-methoxypyridine, the common compound, a new synthetic route is introduced below. name: 2-Amino-4-methoxypyridine

2-Amino-4-methoxypyridine (1.24 g, 10 mmol) was dissolved in 100 mL of acetic acid, After cooling to 0 degrees, A solution of bromine (1.92 g, 12 mmol) in acetic acid (30 mL) was added dropwise. Dropping is completed, The solution is reacted at 30 degrees. 4h, TLC monitoring raw material has been completely reacted, To the reaction solution was added 40 mL of saturated aqueous sodium sulfite solution, 25 degrees stirring reaction 0.5h, Concentrated under reduced pressure, The residue was extracted with ethyl acetate (150 mL ¡Á 3) Dried over anhydrous sodium sulfate, filter, The filtrate was concentrated under reduced pressure, Column chromatography (V (methylene chloride) / V (methanol) = 20/1), Obtained as a light yellow solid (1.45 g, 73%).

The synthetic route of 10201-73-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; Zhen, Changchun; Liu, Bing; Zhang, Weihong; Zhang, Yingjun; Long, Bohua; (59 pag.)CN104513257; (2017); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 947249-14-1, 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.947249-14-1, name is 3-(Difluoromethoxy)pyridin-2-amine, molecular formula is C6H6F2N2O, molecular weight is 160.1215, as common compound, the synthetic route is as follows.

To a solution of 3-(difluoromethoxy)pyridin-2-amine (2.3 g, 14.36 mmol) in acetonitrile (15 mL) was added N-bromosuccinimide (2.61 g, 14.65 mmol) over 3 mm at 0 C. The reaction mixture was stirred at the same temperature for another 20 mm and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (3 x 60 mL). The combined organic layers were driedover sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 20% ethyl acetate in hexane) affording 5-bromo-3-(difluoromethoxy)pyridin-2-amine (3.2 g, 93%): 1H NMR (400 MHz, DMSO-d6) oe: 7.89 (s, 1H), 7.51 (s, 1H), 7.16 (t, I = 73.6 Hz, 1H), 6.34 (s, 2H).

Statistics shows that 947249-14-1 is playing an increasingly important role. we look forward to future research findings about 3-(Difluoromethoxy)pyridin-2-amine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; LYSSIKATOS, Joseph P.; LIU, Wen; SIU, Michael; ESTRADA, Anthony; PATEL, Snahel; LIANG, Guibai; HUESTIS, Malcolm; CHEN, Kevin; WO2015/91889; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13958-98-0, 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. 13958-98-0, name is 3-Bromo-4-cyanopyridine, molecular formula is C6H3BrN2, 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.

1008741 Step C: Preparation of 3-cyclobutylisonicotinonitrile: Charged a dry round bottomed flask plus stir bar with 3-bromoisonicotinonitrile (6.1 g, 33 mmol), anhydrous THF (150 mL), dicyclohexyl(2?,6?-dimethoxy-[ 1,1 ?-biphenyl] -2-yl)phosphine ?S-Phos? (1.0 g, 2.5 mmol), and Pd(OAc)2 (0.37 g, 1.7 mmol). Purged the reaction mixture with N2. Added cyclobutylzinc(II) bromide (100 mL, 50 mmol; 0.5 M in THF) over 15 minutes via cannula. Stirred the reaction mixture for 2 hours at ambient temperature. Partioned mixture between EtOAc (200 mE) and water (200 mE), and filtered through Celite to remove insoluble solids, rinsing with EtOAc. Separated phases, and re-extracted aqueous phase with EtOAc (100 mL). The combined organic phases were washed with brine (150 mL), dried (MgSO4), filtered, and concentrated. The crude material was purified by Biotage Flash 65 silica gel column, eluting with a gradient of 10% EtOAc/hexanes to 1:1 EtOAc/hexanes. Yield: 2.3 g (43%).

According to the analysis of related databases, 13958-98-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA INC.; BLAKE, James F.; BRANDHUBER, Barbara J.; HAAS, Julia; NEWHOUSE, Brad; THOMAS, Allen A.; WINSKI, Shannon L.; WO2014/78331; (2014); 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.98198-48-2, name is 2-Amino-5-bromo-4-methylpyridine, molecular formula is C6H7BrN2, molecular weight is 187.04, as common compound, the synthetic route is as follows.HPLC of Formula: C6H7BrN2

Nitric acid (0.7 ml) was added dropwise to a solution of 5-bromo-4-methylpyridine-2-amine (2.0 g) in concentrated sulfuric acid (8.7 ml) at 55 C. over 30 minutes, and the mixture was stirred at the same temperature for 3 hours. After further stirring at room temperature for 2 hours, the reaction solution was poured into ice water. A 50% aqueous sodium hydroxide solution was added, and the resulting precipitate was collected by filtration, washed with distilled water and then dried under reduced pressure to give the title compound (2.5 g).MS (ESI) m/z: 268 (M+H)+.1H-NMR (CDCl3) delta: 2.54 (3H, s), 5.83 (2H, brs), 8.29 (1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98198-48-2, 2-Amino-5-bromo-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Daiichi Sankyo Company, Limited; US2011/82138; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem