Month: October 2020

651734-54-2, Adding a certain compound to certain chemical reactions, such as: 651734-54-2, name is 2,6-Difluoro-3,5-dimethoxyaniline, 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 651734-54-2.

In a 500-mL round bottom flask, 3.00 g (15.86 mmol) of 2,6-difluoro- 3,5-dimethoxy-phenylamine and 3.13 g (15.86 mmol) of 4-ethylamino-2-methylsulfanyl- pyrimidine-5-carbaldehyde in 150 ml_ of toluene with 1.11 g (4.76 mmol) of camphorsulfonic acid was fitted with a Dean Stark trap and heated at reflux. During the day, the toluene was drained 3 times from the finger, replenished with 100 mL of the solvent and continued heating at reflux under nitrogen atmosphere overnight. The toluene was concentrated in vacuo and dried to give 7.19 g (quantitative) of the title compound. No further purification was necessary. MS (APCI) (m+1)/z 369.1.

According to the analysis of related databases, 651734-54-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2006/38112; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

2062-98-8, 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. 2062-98-8 name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, This 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.

Example 11 A mixture of ethanolamine (13 g, 28 mmole) and ether (30 mL) was cooled to 15 C. Perfluoro-2-methyl-3-oxahexanoyl fluoride (33 g in ether 50 mL) was added dropwise to keep the reaction temperature below 25 C. After the addition, the reaction mixture was stirred at room temperature for one hour. The solid was removed by filtration and the filtrate was washed with hydrochloric acid (0.5N, 30 mL), water (2 times 30 mL), sodium hydrogen carbonate solution (0.5N, 20 mL), water (30 mL), and sodium chloride solution (saturated, 20 mL). It was then concentrated and dried in vacuum over night at room temperature to give a white solid 35 g, yield 95%. H NMR (CDCl3) 1.67 (br s, 1H), 3.57 (m, 2H), 3.80 (t, J=5 Hz, 2H), 6.91 (br s, 1H) ppm. F NMR (CDCl3) -81.2 (dm, J=148 Hz, 1F), -81.7 (t, J=7 Hz, 3F), -82.7 (d, J=3 Hz, 3F), -85.2 (dm, J=148 Hz, 1F), -130.1 (s, 2F), -133.2 (m, 1F) ppm. The product is N-(perfluoro-2-methyl-3-oxahexanoyl)-2-aminoethanol.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Perfluoro(2-methyl-3-oxahexanoyl) fluoride, and friends who are interested can also refer to it.

Reference:
Patent; E.I.DU PONT DE NEMOURS AND COMPANY; US2010/233419; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

62257-15-2,Some common heterocyclic compound, 62257-15-2, name is 2-Fluoro-5-methoxyaniline, molecular formula is C7H8FNO, 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.

Example 3: 2-(2-Fluoro-5-methoxv-phenvlamiotano-4-(2-methanesulfonvl-phenylamiotano)- py?miotadiotane-5-carboxyliotac acid amide (3); Step a: 2-(2-Fluoro-5-methoxy-phenylamiotano)-6-oxo-1 ,6-diotahydro-rhoy?miotadiotane-5-carboxyliotac acid ethyl ester (3a); A mixture of 2-methylsulfonyl-6-oxo-1 ,6-diotahydro-py?miotadiotane-5-carboxyliotac acid ethyl ester (CA Reg No 53554-29-3, 108 mg) and 2-fluoro-5-methoxy-aniotaliotane (CA Reg No 62257-15-2, 90 mg) is heated without solvent in an oil bath of 160 0C After 2h the reaction is cooled, and the residue is crystallized from methanol affording 3a (UPLC method C, tret 1 93 mm, MS 308/ES+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Fluoro-5-methoxyaniline, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2008/9458; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

1515-89-5, 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. 1515-89-5, name is 1-Bromo-3-(methoxymethyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Reference Example 3 (2S)-3-(3-methoxymethylphenyl)propan-1,2-diol To a solution of the compound prepared in reference example 2 (19.5 g) in THF (10 ml) was added acetic acid (80 ml) and water (10 ml) and the mixture was heated to 60 C and stirred for 6 hours. To the mixture was added water (40 ml) and the mixture was cooled to room temperature, and the precipitate was removed by filtration. The filtrate was concentrated. The precipitate was removed again and the mixture was concentrated. From the obtained oil, the solvent was separated as azeotropic mixture with toluene to give the title compound (8.9 g) having the following physical data. TLC: Rf 0.64 (ethyl acetate: hexane = 2: 1).

The synthetic route of 1515-89-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; EP1114816; (2001); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

36942-56-0, These common heterocyclic compound, 36942-56-0, name is 2-Bromo-4-methoxy-1-methylbenzene, 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.

A solution of compound 1 (120 g, 0.59 mol, 1.0 equiv, F-chemicals), compound 2 (101.4 g, 0.65 mol, 1.1 equiv, combi blocks) and potassium carbonate (247.1 g, 1.79 mol, 3.0 equiv) in 1,4-dioxane (2.0 L) and H2O (500 mL) was degassed with N2 for 15 min. Pd(PPh3)4 (34.4 g, 0.029 mol, 0.05 equiv) was added and the mixture was again degassed with N2 gas for 5 min. The reaction mixture was heated at 90 C. for 3 h. The reaction mass was cooled to RT, diluted with ethyl acetate (2.0 L) and washed with brine (1.0 L). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to get the crude material which was purified by column chromatography (silica gel 60-120 mesh, elution 1% EtOAc/Hexane) to get the pure compound 3 (110 g, 79%). TLC solvent system: heptane, Product Rf: 0.5. 1H NMR (300 MHz, Chloroform-d) delta 7.40-7.29 (m, 3H), 7.26-7.14 (m, 2H), 6.85 (dd, J=8.4, 2.7 Hz, 1H), 6.77 (d, J=2.6 Hz, 1H), 3.81 (s, 3H), 2.19 (s, 3H).

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 36942-56-0.

Reference:
Patent; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

93919-56-3, A common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, molecular formula is C8H8F3NO, 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.

EXAMPLE 81 N-1H-indol-4-yl-N’-[4-(trifluoromethoxy)benzyl]urea 4-(Trifluoromethoxy)benzylamine (0.21 g, 1.1 mmol) and the product of Example 80A (0.16 g, 1 mmol) were treated as described in Example 80B to provide the title compound (0.23 g). mp 177 C.; 1H NMR (300 MHz, DMSO-d6) delta 4.36 (d, 2H), 6.52 (m, 1H), 6.95 (m, 3H), 7.24 (t, 1H), 7.36 (d, 2H), 7.48 (d, 2H), 7.63 (dd, 1H), 8.32 (1H), 11.06 (s, 1H); MS (DCI+) m/z 349.9 (M+H)+; Anal. Calcd. For C17H14N3F3O2: C, 58.63, H, 4.34, N, 12.07. Found: C, 58.51, H, 3.98, N, 12.03.

The synthetic route of 93919-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abbott Laboratories; US6933311; (2005); B2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, 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 1462-37-9, 1462-37-9

Example 38d methyl 3-(2-(benzyloxy)ethoxy)-5-methoxybenzoate To a solution of methyl 3-hydroxy-5-methoxybenzoate (Chakraporty, T. K. and Reddy, G. V. J. Org. Chem., 57, 1992, 5462.) (3.3 g, 18.1 mmol) in dry DMF (30 mL) was added K2CO3 (6.3 g, 45.3 mmol) at room temperature. The reaction was stirred at room temperature for 10 minutes then ((2-bromoethoxy)methyl)benzene (3.4 mL, 21.7 mmol) was added and the mixture stirred at 160 C. for 2 hrs. The reaction was cooled down to room temperature and diluted with EtOAc, washed with water and brine, and dried over MgSO4, filtered and concentrated to give the crude product (90%) which was used in the next step without further purification.

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, ((2-Bromoethoxy)methyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SENOMYX, INC.; US2012/41078; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

36805-97-7, These common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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.

2-Chloro-6-methoxymethyl-isonicotinic acid (3.48 g, 15.5 mmol, 1 eq) is dissolved in toluene (60 ml), and the solution is heated to 800C. N,N-dimethylformamide-di-tert-butylacetal (7.53 ml, 31 mmol, 2 eq) is added in portions over 8 h. The reaction mixture is then diluted with TBME and washed with aq NaHCO3. The organic layer is dried over sodium sulfate, filtered and concentrated to give the product.MS (ES+): 258 = [M+H]+. .HPLC (Nucleosil C18HD, 4×70 mm, 3 mum, 5-100% MeCN (6 min), 100% MeCN (1.5 min)) retention time: 6.24 min.

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 36805-97-7.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/77004; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

20781-20-8, 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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 2-chloro-6-(2-furyl)-5-pyrimidin-4-ylnicotinonitrile (0.99 g, 3.50 mmol), 3,4- dimethoxybenzylamine (1.19 g, 7.12 mmol) and triethylamine (0.385 g, 3.80 mmol) in ethanol (13 rill) was heated at 175 C for 50. minutes in Biotage Initiator Microwave Synthesizer. The mixture was then poured into water and extracted with ethyl acetate. The organic layer was dried (MgS04) and evaporated. The resultant oil was taken up in dichloromethane (45 mL), polymer supported benzaldehyde resin (4.82 g, 6.03 mmol of active aldehyde residues) was added and the mixture was shaken overnight. The mixture was filtered and the resin was washed with tetrahydrofuran. The combined filtrate and washings were evaporated to give the title compound (1.50 g, 100%) as an oil. 8 1H NMR (CDCl3) : 9.25 (d, 1 H), 8.60 (d, 1 H), 7.98 (s, 1 H), 7.30 (m, 2H), 7.10 (m, 2H), 6.50 (m, 3H), 6.00 (t, 1 H), 4.75 (d, 2H), 3.90 (s, 3H), 3.85 (s, 3H). ESI/MS (m/e, %) : 414 [(M+1) +, 100].

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:
Patent; ALMIRALL PRODESFARMA, SA; WO2005/100353; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

150-78-7, The chemical industry reduces the impact on the environment during synthesis 150-78-7, name is 1,4-Dimethoxybenzene, I believe this compound will play a more active role in future production and life.

To a solution of 1,4- dimethoxybenzene Q-8 (7.5 g, 53.57 mmol) in acetic acid (25 mL) was added a solution of bromine (17.4 g, 108.9 mmol) in acetic acid (5 mL) at room temperature. After stirring for 2h, the solution was cooled to 10 0C. The resulting fine precipitate was filtered, washed with water (20 mL), and dried under vacuum to obtain compound Q-9 (1Og, 63%) as a white solid. TLC Rf = 0.5 (petroleum ether – EtOAc, 9.9:0.1); 1H NMR (CDCl3) delta 7.10 (s, 2H), 3.84 (s, 6H).

The chemical industry reduces the impact on the environment during synthesis 1,4-Dimethoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; DJABALLAH, Hakim; ANTCZAK, Christophe; WO2010/129049; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem