Month: July 2021

Some common heterocyclic compound, 35896-58-3, name is 1,2,3,4-Tetramethoxy-5-methylbenzene, molecular formula is C11H16O4, 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. Recommanded Product: 1,2,3,4-Tetramethoxy-5-methylbenzene

Step 3a: Synthesis of 1-Bromo-2,3,4,5-tetramethoxy-6-methyl benzeneTo a stirred solution of l,2,3,4-tetramethoxy-5-methylbenzene (obtained in Step 2a) (1.60 g, 7.54 mmol) in DCM (50 mL), a solution of bromine (0.41 mL, 7.92 mmol) in DCM (15 mL) was slowly added, and the resulting mixture was stirred at room temperature for 1 h. Water was added, the organic layer was separated and washed with 1 M NaOH and brine. The combined organic layers were dried over sodium sulphate and concentrated to dryness to give the product as yellow oil (2.00 g, 91%).Yield: 91%. TLC: R/= 0.80 petroleum ether:EtOAc 90:10 v/v. Spectroscopic data were as those reported in the literature by Tremblay, M. S. et al, Org. Lett. 2005, 7, 2417

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 35896-58-3, its application will become more common.

Reference:
Patent; NICOX SCIENCE IRELAND; BLANGETTI, Marco; FRUTTERO, Roberta; GASCO, Alberto; GIORGIS, Marta; LAZZARATO, Loretta; ROLANDO, Barbara; ALMIRANTE, Nicoletta; STORONI, Laura; WO2015/155234; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 702-24-9, 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. 702-24-9, name is 4-Methoxy-N-methylbenzylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of Ph3P (3148 mg, 12 mmol, 1 equiv) and hexachloroethane (2982 mg, 12.6 mmol, 1.05 equiv) in CHCl3 (total volume 40 mL) was stirred at 65 °C for 8 h. After cooling to r.t., under N2, to the mixture was added saccharin (7690 mg, 42.0 mmol, 3.5 equiv) in one portion, followed by the addition of the stock solution of DIPEA in CHCl3 (1.32 M, 59 mL, 78 mmol, 6.5 equiv). The resulting mixture was heated under N2 at 60 °C for 6 h. The mixture was cooled to r.t. and filtered under N2. The solid crude was washed with CHCl3 (3 × 5 mL) and dried under vacuum. The dry solid (5410 mg) was kept under N2. No further separation was attempted, and the resulting solid was used directly in the parallel chemistry. The total yield from Ph3P to the solid was assumed to be 100percent, thus the theoretical amount of the ?active? mixture of 13 and 14 was 451 mg/mol. Parallel Chemistry; General Procedure (Scheme 5) Under N2, to a mixture of the dry solid 13/14 (226 mg, 0.5 mmol) was added a stock solution of DIPEA (1.5 M, 2.17 mL, 3.25 mmol, 6.5 equiv) in CHCl3 at r.t. The mixture was stirred at r.t. for 5 min before a solution of the appropriate amine (1.0 mmol, 2 equiv) in CHCl3 (2 mL) was added. If the amine was in the form of HCl salt, 1 equiv extra of DIPEA was added to the reaction mixture. The resulting mixture was stirred at r.t. for 20 h, and then heated at 60 °C for 15 min. The solvents were evaporated, and the dry residue was dissolved in DMSO (4 mL). The DMSO solution was submitted to purification group for isolation.

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, 4-Methoxy-N-methylbenzylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Yantao; Aurell, Carl-Johan; Korsgren, Pernilla; Malm, Johanna; Haerslaett, Malin; Friden-Saxin, Maria; Pettersen, Anna; Synthesis; vol. 50; 7; (2018); p. 1471 – 1481;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 19500-02-8,Some common heterocyclic compound, 19500-02-8, name is 3-Methoxy-2-methylaniline, molecular formula is C8H11NO, 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 stirred solution of amine 2 (42.58 g, 0.31 mol) and di-tert-butyl dicarbonate (65.48 g, 0.30 mol) in THF (300 mL) was heated to maintain reflux for 4 h. After cooling to RT, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc (500 mL). The resultant solution was washed with 0.5 M citric acid (2.x.100 mL), water (100 mL), saturated aqueous NaHCO3 (200 mL), brine (200 mL) and dried over MgSO4. After filtration and removal of the solvent from the filtrate, the residue (red oil, 73.6 g) was dissolved in hexanes (500 mL) and filtered through a pad of Silica Gel (for TLC). The filtrate was evaporated under reduced pressure to provide N-Boc aniline 3 as a yellow solid. Yield: 68.1 g (96percent).

The synthetic route of 19500-02-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-methoxyaniline, molecular formula is C7H8BrNO, 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. category: ethers-buliding-blocks

Example 57A (102mg, 0.50 mmol) was treated with concentrated HCl (10 mL), cooled to 0 C, treated with a solution OF NAN02 (45MG, 0.65 mmol) in H20 (5 mL), stirred at 0 C for 1 hour, treated with a solution of KI (249mg, 1.5 mmol) in H20 (5 mL), stirred overnight while warming to room temperature, and extracted with ethyl acetate. The extract was washed with H20 and 10% Na2S203, dried (MGS04), filtered, and concentrated to provide 147mg (94%) of the desired product. MS (ESI) m/e 332 (M+20) + ; LH NMR (300 MHz, DMSO-d6) 8 7.39 (d, J = 1. 87 Hz, 1H), 7.34 (d, J = 8. 11 HZ, 1H), 7.24 (dd, J = 8. 11,1. 87 HZ, 1H), 3.86 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19056-40-7, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/76424; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, belongs to ethers-buliding-blocks compound, 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 1535-73-5, SDS of cas: 1535-73-5

General procedure: An equimolar mixture of trifluoromethoxyaniline 1 or 2 (5.65 mmol) and the corresponding activated enol ether 3a-h was heated under reflux for 2-120 min (TLC detection). If necessary, methanol or ethanol was used as solvent. Once the reaction was complete, it was cooled to room temperature and the solids formed were separated by suction, washed with hexanes and dried to give enamines 4-5a-h. Isolated enamines 4-5a-h were characterized and used in the subsequent steps.

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.

Reference:
Article; Plevova, Kristina; Briestenska, Katarina; Colobert, Francoise; Mistrikova, Jela; Milata, Viktor; Leroux, Frederic R.; Tetrahedron Letters; vol. 56; 36; (2015); p. 5112 – 5115;,
Ether – Wikipedia,
Ether | (C2H5)2O – 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. 102503-23-1, name is 1-(2,4-Dimethoxyphenyl)-N-methylmethanamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H15NO2

General procedure: N-(2,4-dimethoxybenzyl)-N-methyl-3-phenylprop-2-yn-1-amine (5a). CuI (20 mg, 0.10 mmol) was added to a solution of phenylacetylene(510.6 mg, 5.0 mmol), HCHO (36% aq., 2 mL),N-methyl(2,4-dimethoxybenzyl)amine (1.09 g, 6.0 mmol) in DMSO (10.0mL). The resulting yellow green solution was stirred at room temperatureovernight and then diluted with H2O (10 mL), extracted with Et2O (15 mL x 3). The combined extractswas washed with H2O (2 x), brine (2 x) respectively, dried over Na2SO4, filtered, concentrated. Theresultant yellow oil was purified through flash column chromatography (silica gel, EtOAc/Hex = 1:6 to1:3) to give the product (5a, 1.14 g, 96%).

According to the analysis of related databases, 102503-23-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Miao; Odelberg, Shannon J.; Tong, Zongzhong; Li, Dean Y.; Looper, Ryan E.; Tetrahedron; vol. 69; 27-28; (2013); p. 5744 – 5750;,
Ether – Wikipedia,
Ether | (C2H5)2O – 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. 702-24-9, name is 4-Methoxy-N-methylbenzylamine, A new synthetic method of this compound is introduced below., Product Details of 702-24-9

Step 2. [(4-Methoxybenzyl)methylamino]acetonitrile PMBN N CN I [00314] A solution of (4-methoxybenzyl)methylamine (125 g, 0.828 mol), chloroacetonitrile (75 g, 0.993 mol, 1.20 equiv) and N,N-diisopropylethylamine (134 g, 1.035 mol) in toluene (600 mL) was refluxed for 1 h. The mixture was cooled to room temperature and diluted with EtOAc (1.5 L). The solution was washed with H20 (3 x 750 mL), brine, dried over Na2S04, filtered and the solution concentrated under reduced pressure. The residual liquid was distilled to give 152 g (97percent) of [(4- methoxybenzyl)methylamino]acetonitrile (bp 128-135°, 2.0 Torr).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; THE UNIVERSITY OF CHICAGO; GAJEWSKI, Thomas F.; SPRANGER, Stefani; LEUNG, Michael; WO2014/66834; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 36865-41-5, 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. 36865-41-5, name is 1-Bromo-3-methoxypropane, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of Mg (911 mg, 37.5 mmol) and of iodine (one crystal) in dry THF (30 mL) was added dropwise 5% of the total amount of 1-bromo-3-methoxypropane (4.59 g, 30.0 mmol). The mixture was heated to reflux with the help of a heat gun until the Grignard formation had started. The rest of the 1-bromo-3-methoxypropane was added slowly, while an exothermic reaction proceeded. After the end of the addition, the reaction mixture was stirred under reflux for 20 min, and was allowed to cool to rt. This Grignard sol. (1M in THF, 23.5 mL, 23.5 mmol) was added dropwise to a mixture of 2-bromo-5-chloro-4-dimethoxymethyl-pyridine (2.50 g, 9.38 mmol) and Ni(dppp)Cl2 (495 mg, 0.938 mmol) in THF (50 mL) at 0 C. The reaction mixture was stirred at rt for 30 min, and was then heated to reflux for 2 h. The mixture was allowed to cool to rt, and was dissolved with EtOAc. This mixture was washed with aq. sat. NaHCO3. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane o EtOAc/heptane 1:1) yielded the title compound (1.51 g, 62%). LC-MS: tR=0.80 min; ES+: 260.15.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3-methoxypropane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Actelion Pharmaceuticals, Ltd.; US2009/88457; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 867288-00-4, These common heterocyclic compound, 867288-00-4, name is 3,5-Difluoro-3′-methoxy-[1,1′-biphenyl]-4-amine, 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.

Procedure -1A solution of an anhydride (1.3 eq.) and an amine (1 eq) were dissolved in dioxane and refluxed overnight. Dioxane was evaporated and the resultant residue dissolved in AcOEt and extracted into aq. 2N NaHC03 solution. The aqueous layer was acidified with aq. 2 HC1 to obtain a solid, which was filtered and dried to give the desired amide.Example 12-(3^-Difluoro-3′-methoxybiphenyl-4-yIcarbainoyI)berizoic acid:The title compound (52 mg) was obtained from intermediate 1 (150 mg, 0.64 mmol) and phthalic anhydride (189 mg) as a white solid. MJ: 168-173G te-NMR (delta ppm, DUSO- k, 400 MHz): 13.05 (s, 1H), 10.19 (s, 1H), 7.83 (d, J 7.4, 1H), 7.69-7.63 (m, 1H), 7.62-7.52 (m, 4H), 7.39 (t, / 7.9, 1H), 7.34-7.27 (m, 2H), 6.98 (d, / 6.8, 1H), 3.83 (s, 3H). MS (m z): 381.55 ([itf-H]”).

The synthetic route of 867288-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INCOZEN THERAPEUTICS PVT. LTD.; RHIZEN PHARMACEUTICALS SA; MUTHUPPALANIAPPAN, Meyyappan; BHAVAR, Prashnant, Kashinath; VISWANADHA, Srikant; VAKKALANKA, Swaroop, Kumar, V.S.; MERIKAPUDI, Gayatri, Swaroop; WO2011/138665; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – 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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

(2S,4R)-4-hydroxy-l-(3-(2-(2-methoxyethoxy)ethoxy)benzoyl)-N-(4-(4-methylthiazol-5- yl)benzyI)pyrrolidine-2-carboxamide A mixture of (2S,4R)-4-hydroxy-l-(3-hydroxybenzoyl)-N-(4-(4-methylthiazol-5- yl)benzyl)pyrrolidine-2-carboxamide (55 mg, 0.13 mmol) and potassium carbonate (55 mg, 0.40 mmol) in DMF (0.8 mL) was treated with l-bromo-2-(2-methoxyethoxy)ethane (commercially available from for example Aldrich) (0.034 mL, 0.25 mmol) and the reaction stirred at 50C for 2.5 hours. Additional l-bromo-2-(2-methoxyethoxy)ethane (0.034 mL, 0.25 mmol) was added and the mixture stirred at 50C overnight. The product was subjected to purification by mass-directed automated preparative HPLC (formic acid modifier) to afford the title compound (40 mg, 0.074 mmol, 59 % yield) LCMS RT= 0.74 min, ES+ve m/z 540 [M+H]+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 54149-17-6.

Reference:
Patent; YALE UNIVERSITY; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CAMBRIDGE ENTERPRISE LIMITED UNIVERSITY OF CAMBRIDGE; CREWS, Craig, M.; BUCKLEY, Dennis; CIULLI, Alessio; JORGENSEN, William; GAREISS, Peter, C.; MOLLE, Inge, Van; GUSTAFSON, Jeffrey; TAE, Hyun-Seop; MICHEL, Julien; HOYER, Dentin, Wade; ROTH, Anke, G.; HARLING, John, David; SMITH, Ian Edward, David; MIAH, Afjal, Hussain; CAMPOS, Sebastian, Andre; LE, Joelle; WO2013/106646; (2013); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem