Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 116026-93-8, tert-Butyl (3-formylpyridin-4-yl)carbamate, 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, name: tert-Butyl (3-formylpyridin-4-yl)carbamate, blongs to pyridine-derivatives compound. name: tert-Butyl (3-formylpyridin-4-yl)carbamate

Example 106: (5Z)-5-[(4-aminopyridin-3-yl)methylidene]-2-(piperidin-l-yl)-4,5-dihydro- l,3-thiazol-4-one hydrochloride; (3-Formyl-pyridin-4-yl)-carbamic acid tert-butyl ester (490mg, 1.5mmol), piperidine (0.30 mL, 3.0 mmol), and rhodanine (203mg, 1.5mmol) were added into 10 mL of ethanol in 5OmL flask. The resulting mixture was heated at 75 0C overnight. The solvent was evaporated, 0 and the crude was purified by flash chromatography (0 to 10% MeOH in DCM gradient). 200 mg of [3 -(4-Oxo-2 -piperidin-l-yl-4H-thiazol-5-ylidenemethyl)-pyridin-4-yl]-carbamic acid tert- butyl ester yellow solid was collected as pure product (yield 34%).[3-(4-Oxo-2-piperidin- 1 -yl-4H-thiazol-5-ylidenemethyl)-pyridin-4-yl]-carbamic acid tert- butyl ester (200mg) was dissolved in 5mL of methanolic HCl (4M). The resulting mixture was 5 stirred at room temperature for 2 hours. The solvent was evaporated, and the remaining solid was dried under vacuum to provide desired product (yield 99%). 1H NMR (400 MHz, DMSO- d6) delta 1.67 (m, 6H), 3.5 (m, 2H), 3.90 (m, 2H), 6.97(d, IH), 7.50 (s, IH), 8.13(d, IH), 8.30 (s, IH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,116026-93-8, tert-Butyl (3-formylpyridin-4-yl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; CHLORION PHARMA, INC.; WO2009/97695; (2009); A1;,
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. 1289093-31-7, name is 5-Bromo-3-chloro-2-isobutoxypyridine, the common compound, a new synthetic route is introduced below. name: 5-Bromo-3-chloro-2-isobutoxypyridine

To a mixture of 6-fluoro-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carbonitrile (step 5) (220 mg, 1.2 mmol) in dioxane (20 ml) was added 5-bromo-3-chloro-2-isobutoxypyridine (intermediate A) (980 mg, 3.7 mmol), CuI (470 mg, 2.5 mmol), K2CO3 (341 mg, 2.5 mmol), and DMEDA (260 mg, 2.5 mmol). After addition, the mixture was degassed and charged with N2 three times. Then the mixture was heated to 110 C. and stirred at that temperature under N2 atmosphere for 16 hrs. When LC/MS indicated the starting material was consumed, the reaction mixture was diluted with DCM (200 ml). The mixture was filtered over celite. The filtration was washed with brine (*3), dried over anhydrous Na2SO4 and filtered. The filtration was evaporated to afford a residue, which was purified by flash column chromatography on silica gel using a gradient 0-20% ethyl acetate in hexanes to afford the title compound as white solid. LC-MS: Rt=1.27 mins; MS m/z [M+H]+ 362.0; Method 5-95AB 1.5minLC_v003 1H NMR (400 MHz, CDCl3) delta 7.96 (1H, d), 7.56 (1H, d), 6.98 (1H, d), 6.22 (1H, d), 4.31 (2H, m), 4.11 (2H, d), 3.68 (2H, m), 2.16 (1H, m), 1.05 (6H, d).

The synthetic route of 1289093-31-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHEN, Shuhui; HE, Haiyang; LAGU, Bharat; QIN, Hua; WU, Chengde; XIAO, Yisong; US2015/183802; (2015); 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. 113237-20-0, name is 2,6-Dichloro-5-fluoronicotinamide. This compound has unique chemical properties. The synthetic route is as follows. name: 2,6-Dichloro-5-fluoronicotinamide

At RT, 44 g (210.58 mmol) of 2,6-dichloro-5-fluo- ronicotinamide were added to a suspension of2l.9 g (335.35 mmol) of zinc in methanol (207 ml). Acetic acid (18.5 ml) was then added, and the mixture was heated at reflux with stirring for 24 h. The contents of the flask were then decanted from the zinc, ethyl acetate (414 ml) and saturated aqueous sodium bicarbonate solution (414 ml) were added and the mixture was stirred vigorously. The mixture was then filtered off with suction through kieselguhr and washed three times with ethyl acetate (517 ml each). The organic phase was separated off and the aqueous phase was washed with ethyl acetate (258 ml). The combined organic phases were washed once with saturated aqueous sodium bicarbonate solution (414 ml), dried and concentrated under reduced pressure. Dichloromethane (388 ml) was added to the crystals obtained in this manner, and the crystals were triturated for 20 mm. The crystals were once more filtered off with suction and washed with diethyl ether and sucked dry.10414] Yield: 20.2 g (53% of theory) ?H NMR (400 MHz, DMSO-d5): oe=7.87 (br s, 1H),7.99 (dd, 1H), 8.10 (br s, 1H), 8.52 (d, 1H).

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, 113237-20-0, 2,6-Dichloro-5-fluoronicotinamide.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Follmann, Markus; Stasch, Johannes-Peter; Redlich, Gorden; Ackerstaff, Jens; Griebenow, Nils; Knorr, Andreas; Wunder, Frank; Li, Volkhart Min-Jian; Kroh, Walter; Baerfacker, Lars; US2014/350020; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 893423-62-6, tert-Butyl (2-chloro-3-formylpyridin-4-yl)carbamate, 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, 893423-62-6, blongs to pyridine-derivatives compound. Application In Synthesis of tert-Butyl (2-chloro-3-formylpyridin-4-yl)carbamate

4-Amino-2-chloronicotinaldehyde (1-5c) Trifluoroacetic acid (17.4 mL, 234 mmol) was added carefully to a stirred mixture of Boc aldehyde 1-4 (20 g, 78.1 mmol) and dichloromethane (60 mL) keeping the temperature below 25 C. The solution was warmed to 35 C., aged overnight (vigorous off-gassing) and then cooled to room temperature. 25 mL of MTBE was added and the resulting white slurry was aged for one hour, filtered, and the filter cake rinsed with MTBE (10 mL*2). Solid 1-5c TFA salt was dried under vacuum.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,893423-62-6, its application will become more common.

Reference:
Patent; Kelly, Michael J.; Layton, Mark E.; Sanderson, Philip E.; US2008/161317; (2008); 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.5349-17-7, name is 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide, molecular formula is C7H7Br2NO, molecular weight is 280.9446, as common compound, the synthetic route is as follows.Application In Synthesis of 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide

[0342] l-(4-{[4-(4-Pyridinyl)-l,3-thiazol-2-yl]amino}phenyl)ethanone (131). A mixture of bromoketone hydrobromide 1 (0.60 g, 2.14 mmol) and 4- acetylphenylthiourea (130) (0.41 g, 2.14 mmol) in EtOH (20 mL) was stirred at reflux temperature for 3 h. The mixture was cooled to 20 0C, diluted with water (50 mL), the pH adjusted to ca. 8 with aqueous NH3 and the mixture stirred at 20 0C for 2 h. The precipitate was filtered, washed with water (5 mL) and dried. The crude solid was purified by column chromatography, eluting with 50% EtO Ac/pet, ether, to give amine 131 (0.40 g, 64%) as a cream powder: mp (EtO Ac/pet, ether) 229-231 0C; 1H NMR delta 10.80 (br s, 1 H, NH), 8.63 (dd, J= 4.5, 1.6 Hz, 2 H, H- 2″‘, H-6′”), 8.01 (br d, J= 8.8 Hz, 2 H, H-2′, H-6’), 7.89 (dd, J= 4.5, 1.6 Hz, 2 H, H-3″‘, H-5″‘), 7.85 (br d, J= 8.8 Hz, 2 H, H-3′, H-5’), 7.82 (s, 1 H, H-5″), 2.53 (s, 3 H, H-2); 13C NMR delta 195.9, 162.5, 150.1 (2), 147.7, 144.8, 140.7, 129.8 (2), 119.8 (2), 116.0 (2), 108.7, 26.1, one carbon not observed. Anal, calcd for Ci6Hi3N3OS: C, 65.06; H, 4.44; N, 14.23. Found: C, 65.11; H, 4.40; N, 14.13%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5349-17-7, 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide, and friends who are interested can also refer to it.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; AUCKLAND UNISERVICES LIMITED; WO2009/114552; (2009); 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.1659-31-0, name is Dipyridin-2-yl carbonate, molecular formula is C11H8N2O3, molecular weight is 216.19, as common compound, the synthetic route is as follows.Computed Properties of C11H8N2O3

Under nitrogen atmosphere, to a stirred mixture of (3S,4R)-2-methyl-4-oxo-3- oxetanylammonium toluene-4-sulfonate (0.100 g, 0.36 mmol) in dry CH2C12 (1 mL), DIPEA (0.060 mL, 0.36 mmol) was added dropwise. Subsequently, the crude mixture containing (1- methyl-5-phenyl-pentyl)-2- oxopyridine 1-carboxylate (0.31 g, 1.02 mmol) dissolved in dry CH2C12 (2 mL) was added. The reaction mixture was stirred 15h at rt, concentrated to dryness and purified by column chromatography using a Teledyne ISCO apparatus, eluting with Cy/TBME (from 100:0 to 70:30). The crude product was further purified by preparative HPLC-MS to afford the title compound (0.035 g, 32%), as a pure mixture (ratio=l : 1) of two diastereoisomers. MS (ESI) m/z: 306 [M-H]+; (ESI) m/z: 304 [M-H] 1HNMR (DMSO-d6): delta 1.12-1.21 (m, 6H), 1.26-1.38 (m, 10H), 1.46-1.64 (m, 8H), 2.52-2.61 (m, 4H), 4.64-4.75 (m, 2H), 4.84 (dq, J= 6.2 Hz, 2H), 5.39 (dd, J= 6.2, 9.3 Hz, 2H), 7.12-7.31 (m, 10H), 8.12 (d, 7= 9.3 Hz, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1659-31-0, Dipyridin-2-yl carbonate, and friends who are interested can also refer to it.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; IIT – ISTITUTO ITALIANO DI TECNOLOGIA; UNIVERSITY DEGLI STUDI DI URBINO; UNIVERSITA DEGLI STUDI DI PARMA; PIOMELLI, Daniele; BANDIERA, Tiziano; MOR, Marco; TARZIA, Giorgio; BERTOZZI, Fabio; PONZANO, Stefano; WO2013/78430; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1149-24-2, 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. 1149-24-2, name is Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate. A new synthetic method of this compound is introduced below.

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 ¡Á 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1149-24-2, its application will become more common.

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

Application of 911434-05-4, 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 911434-05-4 as follows.

N,N-Dimethylformamide (270 kg), 5-bromo-2-methyl-3-nitropyridine (90.0 kg, 415 mol), and N,N-dimethylformamide dimethyl acetal (108.0 kg, 906.3 mol) were added to a 2000 L vessel at RT. The reaction mixture was stirred at RT for 30 minutes, then heated to 90¡À5C over a 3 -hour period and maintained at this temperature for 4 hours. The mixture was subsequently cooled to 25¡À5C. Water (945 kg) was added while keeping the temperature of the mixture at 25¡À5C. After the addition of water, the reaction mixture was stirred for 2 hours. The solids were centrifuged to obtain wet product, which was slurried in isopropanol (207 kg) for 1 hour at 25¡À5C. The solids were centrifuged again to obtain the title compound as a wet solid (105 kg, 92.5 wt % assay). The product was used in the next step without additional drying

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,911434-05-4, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; CHANG, Edcon; NOTZ, Wolfgang Reinhard Ludwig; WALLACE, Michael B.; WO2014/11568; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 351227-42-4, Adding some certain compound to certain chemical reactions, such as: 351227-42-4, name is 6-Chloro-4-iodopyridin-3-amine,molecular formula is C5H4ClIN2, 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 351227-42-4.

Route B : A mixture of 6-chloro-4-iodopyridin-3-ylamine (Preparation 8, 0.33g, 1.30mmol), pyruvic acid (0.27mL, 3.89mmol), DABCO (0.44g, 3.89mmol) and palladium acetate (0.015g, 0.07mmol) in dry DMF was stirred vigorously and degassed with argon for 15min. The reaction mixture was heated to 1070C for 5h. The reaction mixture was allowed to cool to rt and stirred for 16h. The volatiles were removed under reduced pressure and the residue partitioned between EtOAc (10OmL) and water (5OmL). The layers were separated and the aqueous extracted with EtOAc (2x50mL). The combined organics were extracted with aqueous NaOH (2M, 3x70mL). The combined aqueous extracts were acidified to pH 4 by careful addition of glacial acetic acid, then extracted with EtOAc (3x60mL). The combined organics were washed with brine (5OmL), dried (MgSO4), filtered and concentrated in vacuo to give the title compound as a brown solid. RT=2.72min, m/z (ES+) =197 [M+ H]+

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 351227-42-4, 6-Chloro-4-iodopyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PROSIDION LIMITED; WO2006/59164; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1124382-72-4, Adding some certain compound to certain chemical reactions, such as: 1124382-72-4, name is 2-Amino-8-bromo[1,2,4]triazolo[1,5-a]pyridine,molecular formula is C6H5BrN4, 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 1124382-72-4.

Intermediate 49 (16 g, 55.92 mmol) and water (75 mL) were added to a sol. of intermediate 51 (7.94 g, 37.28 mmol) in DME (200 mL). Then, Pd(PPh3)4 (4.31 g, 3.73 mmol) was added and the r.m. was stirred at 150 C for 10 min. under microwave irradiation. The mixture was filtered through diatomaceous earth and concentrated in vacuo. The crude product was purified by flash column chromatography (silica; eluent: DCM/(7 N NH3 in MeOH) from 100/0 to 97/3). The product fractions were collected and the solvent evaporated in vacuo to yield 7 g of a first fraction of intermediate 52. The impure fractions were also collected, evaporated in vacuo and the crude product was purified by RP preparative HPLC [RP Vydac Denali CI 8 (10 mm, 250 g, 5 cm); mobile phase: 0.25% NH4HC03 sol. in water/CH3CN]. The product fractions were collected and the solvent evaporated in vacuo. The crude product was further purified by RP preparative SFC [Diol; mobile phase: C02, MeOH (with 0.2% isopropylamine)]. The product fractions were collected and the solvent evaporated in vacuo to yield 4 g of a second fraction of intermediate 52. Yield: 11 g of intermediate 52 (quantitative yield).

According to the analysis of related databases, 1124382-72-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; MINNE, Garrett, Berlond; BISCHOFF, Francois Paul; GIJSEN, Henricus, Jacobus, Maria; VELTER, Adriana, Ingrid; PIETERS, Serge, Maria, Aloysius; BERTHELOT, Didier, Jean-Claude; WO2013/10904; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem