Month: November 2020

1462-37-9, The chemical industry reduces the impact on the environment during synthesis 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, I believe this compound will play a more active role in future production and life.

step Bl – Ethyl phenylcyanoacetate (22, 18.3 mL, 0.1054 mol, Ar1 = Ph) was added dropwise to a suspension of NaH (4.85 g, 0.1213 mol, 60percent dispersion in oil) in DMF (200 mL) cooled to 0 C. The resulting mixture was stirred at 0 C for 30 min then benzyl 2-bromoethyl ether (20 mL, 0.1265 mmol) was added. The reaction mixture was then stirred at 60 C overnight, cooled to RT and partitioned between EtOAc and a saturated aqueous NH4Cl. The aqueous layer was thrice back- extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by Si?2 chromatography eluting with a EtOAc/hexane gradient (5 to 95percent EtOAc) to afford 20 g (60percent) of 24a.

The chemical industry reduces the impact on the environment during synthesis ((2-Bromoethoxy)methyl)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; LEMOINE, Remy; MELVILLE, Chris Richard; ROTSTEIN, David Mark; WANNER, Jutta; WO2008/34731; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

A common compound: 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 20781-20-8

b) 3-[2-(2,4-dimethoxybenzylamino)pyridin-4-yl]-/V-(1-methylpiperidin-4- yl)imidazo[1,2-b]pyridazin-6-amineTo a solution of 3-(2-chloropyridin-4-yl)-//-(1-methylpiperidin-4-yl)imidazo[1 ,2-b]pyridazin-6- amine (100 mg, 0.29 mmol) and NaO’Bu (39 mg, 0.41 mmol) in DME (2 mL) was added a pre-mixed solution of Pd(OAc)2 (3 mg, 0.015 mmol) and CyPF-‘Bu (8 mg, 0.015 mmol) in DME (1 mL). The reaction mixture was stirred for 5 min before 2,4-dimethoxybenzylamine (68 mg, 0.41 mmol) was added and the mixture heated at 100C for 18 h. The reaction mixture was concentrated in vacuo and purification by column chromatography (EtOAc-2M NH3 in MeOH gradient) gave an off-white solid (77 mg, 56%); 1H NMR (400 MHz, CD3OD) delta ppm 7.94 (d, J=6.0 Hz, 1H), 7.85 (s, 1 H), 7.62 (d, =9.6 Hz, 1 H), 7.51 (s, 1 H), 7.24 (dd, J=5.7, 1.6 Hz, 1H), 7.21 (d, J=8.2 Hz, 1 H), 6.72 (d, J=9.6 Hz, 1 H), 6.54 (d, J=2.3 Hz, 1 H), 6.46 (dd, J=8.2, 2.3 Hz, 1H), 4.43 (s, 2H), 3.83 (s, 3H), 3.82-3.76 (m, 1H), 3.75 (s, 3H), 2.88-2.77 (m, 2H), 2.23-2.09 (m, 7H), 1.68-1.53 (m, 2H); m/z (ES+APCI)+: 474 [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, 20781-20-8, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; OSBORNE, Simon; CHAPMAN, Timothy; LARGE, Jonathan; BOULOC, Nathalie; WALLACE, Claire; WO2011/101640; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

588-96-5, Adding a certain compound to certain chemical reactions, such as: 588-96-5, name is p-Bromophenetole, 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 588-96-5.

General procedure: A mixture of aryl halide (0.25 mmol), phenylboronicacid (0.3 mmol), Na2CO3 (0.25 mmol), PPh3 (0.025 mmol)and Pd(at)PAAs-CD (0.5 mg, 0.2 mol% Pd per mol of arylhalide) were placed into a 10 mL Schlenck tube with1 mL H2O. The reaction mixture was reacted at 80 C for18 h, and the reaction progress was monitored via gaschromatography mass spectrometry (GC-MS). The reactionmixture was allowed to cool to room temperature, andthen 3 mL water was added, and the product was extractedwith ethyl acetate (3 mL ¡Á 3). The organic layers werecombined and dried over anhydrous Na2SO4 and solventswere evaporated via rotary evaporator. The crude productwas purified by column chromatography (200-300 meshsilica) using a mixture of petroleum ether/ethyl acetate(10:1, v:v) as eluent. The structures of the products wereconfirmed by 1H NMR and 13C NMR spectroscopies.

According to the analysis of related databases, 588-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Wei; Yao, Zi-Jian; Deng, Wei; Journal of the Brazilian Chemical Society; vol. 30; 8; (2019); p. 1667 – 1677;,
Ether – Wikipedia,
Ether | (C2H5)2O – 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. 6346-09-4, name is 4,4-Diethoxybutan-1-amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 6346-09-4

Amine 1 (Aldrich) (3. 5g, 21.7 mol) was dissolved in a mixture of chloroform (30 ml) and IN sodium hydroxide (24 ml) and [15ML] of mesitylenesulfonyl chloride dissolved in [1 SML] of chloroform were added at [5C.] The mixture was stirred for 2h, the reaction mixture was then diluted with chloroform (50 ml), the organic layer was separated, washed with a saturated solution of ammonium chloride, dried [(NA2S04),] and evaporated to dryness. The residual oil crystallized after drying and was used in the next step without further purification; 7. 0g (95%) of 2 were obtained [;’HNMR (CDC13)] : [PPM] 1.15 (t, 6H), 1.55 (m, 4H), 2.30 (s, 3H), 2.65 (s, 6H), 2.95 (q, 2H), 3.40-3. 55 [(M,] 4H), 4.40 (t, 1H), 4.90 (t, 1H), 6.95 (s, 2H) [; 13CNMR (CDCL3)] : [PPM] 15.19, 20.80, 22.85, 24.55, 30.83, 42.39, 61.40, 102.41, 131.84, 133.82, 138.99, 141.92.

The synthetic route of 6346-09-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SLIL BIOMEDICAL CORPORATION; WO2004/2991; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

398-62-9, A common heterocyclic compound, 398-62-9, name is 4-Fluoro-1,2-dimethoxybenzene, molecular formula is C8H9FO2, 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.

To a suspension of sulfur trioxide N,N-dimethylformamide complex (4.108 g, 27 mmol) in 1,2-dichloroethane was added 4-fluoroveratrole (3.49 g, 22 mmol) dropwise. The mixture was slowly heated to 85 C. in an oil bath. After 2.5 h, the solids had dissolved to afford a golden yellow solution. A trace of starting material was still present and heating was continued for a further 4.5 h. The oil bath was removed and thionyl chloride (1.95 ml, 27 mmol) added dropwise. The mixture was heated 4 h at 85 C. and allowed to cool to room temperature. The solution was poured into water and extracted with dichloromethane (3¡Á50 ml), the combined organics washed with water, dried over magnesium sulfate and evaporated. Remaining traces of N,N-dimethylformamide were removed azeotropically with toluene to afford the product as an off-white solid that was used without further purification. EI MS: m/e=254.0 ([M]+).

The synthetic route of 398-62-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Plancher, Jean-Marc; Taylor, Sven; US2005/165012; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – 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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 20781-20-8

General procedure: The solution of l-(benzyloxy)-6-bromo-3-((2,4-difluorobenzyl)carbamoyl)-2-oxo-l,2-dihydro-l,8- naphthyridin-4-yl 4-methylbenzenesulfonate (7; 0.2 mmol), N-ethyl-N-isopropylpropan-2-amine (2.0 mmol) and amine (1.0 mmol) in DMF (2.0 mL) was heated to 50 C for 1 hr. The reaction mixture was cooled to room temperature and purified by Combiflash. Compound 4-substituted l-(benzyloxy)-6-bromo- N-(2,4-difluorobenzyl)-2-oxo-l,2-dmydro-l,8-naphthyridine-3-carboxamide (8) was afforded.According to general procedure A, the title compound was prepared in 89 % yield from l-(benzyloxy)-6- bromo-3-((2,4-difluorobenzyl)carbamoyl)-2-oxo-l,2-dihydro-l,8-naphthyridin-4-yl 4- methylbenzenesulfonate (7). NMR (400 MHz, CDCI3) delta 12.05 (t, 7 = 6.2 Hz, 1H), 10.61 (t, 7 = 5.7 Hz, 1H), 8.58 (d, 7 = 2.1 Hz, 1H), 8.34 (d, 7 = 2.2 Hz, 1H), 7.57 (dd, 7 = 7.3, 1.9 Hz, 2H), 7.39 – 7.22 (m, 4H), 7.17 (dd, 7 = 8.9, 4.3 Hz, 1H), 6.85 – 6.63 (m, 2H), 6.47 – 6.34 (m, 2H), 5.15 (s, 2H), 4.64 (d, 7 = 6.3 Hz, 2H), 4.52 (d, 7 = 5.7 Hz, 2H), 3.74 (s, 3H), 3.73 (s, 3H)

The synthetic route of 20781-20-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; ZHAO, Xue, Zhi; SMITH, Steven; METIFIOT, Mathieu, A.; JOHNSON, Barry; MARCHAND, Christophe; HUGHES, Stephen; POMMIER, Yves; BURKE, Terrence, R.; WO2014/186398; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

702-24-9, Adding a certain compound to certain chemical reactions, such as: 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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 702-24-9.

General procedure: A solution of N-heterocycle compound (0.2 mmol) and graphene oxide (GO) (8 mg) in N,N-dimethylformamide(1.0 mL) was stirred in a sealed tube under an atmosphere of argon at 150 ¡ãC for 18 h. After being cooled to room temperature,the reaction mixture was filtered and washed with ethyl acetate (20 mL). Afterward, 10 mL water was added tothe solution and extracted with ethyl acetate (3 ¡Á 15 mL), the combined organic layers were dried over anhydrous Na2SO4.The solvent was evaporated under vacuum and the crude product was purified by preparative thin-layer chromatography (TLC) on silica gel with petroleum ether and ethyl acetate to achieve the pure product.

According to the analysis of related databases, 702-24-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ma, Juan; Zhang, Jingyu; Zhou, Xiao; Wang, Jiawei; Gong, Hang; Journal of the Iranian Chemical Society; vol. 15; 12; (2018); p. 2851 – 2860;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

5905-69-1, These common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, 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.

(Reference Example 71) Ethyl 1-[4-(difluoromethoxy)phenyl]piperidine-4-carboxylate[0521] Sodium tert-butoxide (2.29 g, 23.8 mmol), palladium(II) acetate (428 mg, 1.91 mmol), and tri-tert-butylphosphine (370 muL, 1.52 mmol) were added to a solution of ethyl piperidine-4-carboxylate (3.52 mL, 22.9 mmol) and 1-bromo-4-(difluoromethoxy)benzene (4.25 g, 19.1 mmol) in toluene (122 mL), and the mixture was stirred at 80C for 30 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate. The obtained organic layer was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate = 100/0 – 90/10] to obtain the title compound (3.17 g, yield: 56%). [0523] 1H-NMR (400 MHz, CDCl3) delta: 7.07-7.00 (2H, m), 6.95-6.87 (2H, m), 6.41 (1H, t, J = 75 Hz), 4.16 (2H, q, J = 7 Hz), 3.61-3.55 (2H, m), 2.84-2.73 (2H, m), 2.47-2.39 (1H, m), 2.08-1.99 (2H, m), 1.95-1.83 (2H, m), 1.27 (3H, t, J = 7 Hz).

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 5905-69-1.

Reference:
Patent; Daiichi Sankyo Company, Limited; KOBAYASHI, Hideki; OHKAWA, Nobuyuki; TAKANO, Daisuke; KUBOTA, Hideki; ONODA, Toshio; KANEKO, Toshio; ARAI, Masami; TERASAKA, Naoki; EP2862861; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

136-90-3, The chemical industry reduces the impact on the environment during synthesis 136-90-3, name is 4-Methoxy-3-methylphenylamine, I believe this compound will play a more active role in future production and life.

Compound 107 3-[[(3S)-tetrahydrofuran-3-yl]sulfamoyl]benzoic acid (270 mg, 1.0 mmol) was dissolved in dichloromethane (5 mL). 3-methyl-4-methoxyaniline (165 mg, 1.2 mmol) and triethylamine (145 mg, 1.4 mmol) were added to the mixture at 20C. The mixture was stirred at 20C for 5 minutes. HATU (456 mg, 1.2 mol) was added and the mixture was further stirred at 20C for 8 hours. The solvent was removed in vacuo and the obtained residue was purified by high performance liquid chromatography (Column: Phenomenex Synergi C18 150*20mm*5um.. A: H2O+0.1%TFA B: MeCN from 30% to 60 % B in A). The product fractions were collected and the organic solvent was evaporated in vacuo. The aqueous layer was neutralized with saturated aqueous NaHCC>3 and extracted with dichloromethane (2 x 10 mL). The combine organic layers was dried over Na2S04 and concentrated in vacuo resulting in compound 107 (135 mg). Method A; Rt: 5.24 min. m/z : 391.3 (M+H)+ Exact mass: 390.1

The chemical industry reduces the impact on the environment during synthesis 4-Methoxy-3-methylphenylamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN R&D IRELAND; LAST, Stefaan Julien; RABOISSON, Pierre Jean-Marie Bernard; ROMBOUTS, Geert; VANDYCK, Koen; VERSCHUEREN, Wim Gaston; WO2014/33170; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-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. 366-99-4

To 124 (1.09 g, 3.5 mmol) dissolved in acetone (25 mL) was added 3-fluoro- p-anisidine (0.54 g, 3.5 mmol) in acetone (5 mL) followed by addition of 2.5 N NaOH (1.4 mL, 3.5 mmol) and water (3.5mL). The reaction mixture was stirred and heated at reflux for 3 hours. The reaction mixture was extracted three times using dichloromethane ; the combined organic layers were washed with brine and dried over potassium carbonate. The sample was filtered, concentrated in vacuo, and the resulting solid was dried overnight under vacuum to yield white solid (E15) (1.332 g,97percent) ; mp194 C ; HPLC: Inertsil ODS 3V C18,40 : 30: 30 v: v: v[KH2P04(0. 01 M, pH 3.2) : CH30H: CH3CN], 264nm,Rt 33.2 min, 97.6percent purity; MS (TOF ES+)mlz 396 (35.0) ; 394 (M+H, 100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 366-99-4, its application will become more common.

Reference:
Patent; REDDY US THERAPEUTICS, INC.; WO2004/26844; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem