Category: ethers-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, 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 74654-07-2, Recommanded Product: 74654-07-2

To a solution of N-((S)-2-((S)-3-aminopyrrolidin-l -yl)-l -phenylethyl)-2-(3,4- dichlorophenyl)-N-methylacetamide (150 mg, 0.37 mmol) in acetonitrile (3 mL) was added mPEG3-NH2 (66 mg, 0.407 mmol) and potassium carbonate (153 mg, 1.1 1 mmol). The mixture was heated to 50 C for 18 hours. After 18 hours, the mixture was concentrated under vacuum and the resulting crude was dissolved in ethyl acetate (10 mL). The organic layer, after washes with aq. ammonium chloride (10 mL), water (10 mL) and brine (10 mL), was dried over anhydrous sodium sulfate and concentrated under vacuum to give the crude compound. The crude compound post purification by column chromatography afforded 2- (3,4-dichlorophenyl)-N-((5)-2-((,S)-3-((2-(2-(2- methoxyethoxy)ethoxy)ethyl)amino)pyrrolidin-l -yl)-l -phenylethyl)-N-methylacetamide as the free base (0.081 g, 40% yield). NMR (500 MHz, CDC13): delta 7.61 (m, 1 H), 7.40-7.27 (m, 7H), 5.22 (m, 1 H), 4.20 (t, 2H), 3.70-3.45 (m, 10H), 3.32 (s, 3H), 3.24 (m, 2H), 3.04 (m, 1 H), 2.79-2.72 (m, 2H), 2.62 (s, 3H), 2.46-2.30 (m, 4H), 1.54- 1 .79 (m, 2H); MS (EI) for C28H39C12N304: 553 (MH+).

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-(2-(2-Methoxyethoxy)ethoxy)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEKTAR THERAPEUTICS; ANAND, Neel, K.; DUARTE, Franco, J.; ZHANG, Wen; REN, Zhongxu; WO2014/210436; (2014); A2;,
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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 332-48-9 as follows. HPLC of Formula: C8H8BrFO

Synthesis of example SC-51:Step 1: [3-(4-Chlorophenyl)-1 -[2-(4-fluoro-phenoxy)-ethyl]-4-methyl-5-(trifluoromethyl)-1 Hpyrrol-2-yl]-morpholin-4-yl-methanone (SC-51)(3-(4-Chlorophenyl)-4-methyl-5-(trifluoromethyl)-1 H-pyrrol-2-yI)(morpholino)methanone [for synthesis see SC-25] (130 mg, 0.349 mmol) was dissolved in dry MeCN (4 mL). The solution was mixed with K2C03 (120 mg, 0.872 mmol) and KI (8.7 mg, 0.052 mmol), followed by addition of 4-fluorophenoxy- ethylbromide (153 mg, 0.697 mmol). The reaction mixture was stirred vigorously at 80 C for 2 d. The temperature was lowered to room temperature; the reaction mixture was combined with the reaction mixture of another identical reaction (starting from 20 mg or 0.054 mmol (3-(4-chlorophenyl)-4-methyl- 5-(trifluoromethyl)-1 H-pyrrol-2-yl)(morpholino)methanone), followed by concentration in vacuo. The residue was used for flash chromatography (silica, gradient heptane/EtOAc, 1:0 -* 1:1). The product was purified by preparative TLC (silica, DCM twice) to result in 60 mg (29%) of SC-51.

According to the analysis of related databases, 332-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; STEINHAGEN, Henning; DAMANN, Nils; SKONE, Philip; HAMLYN, Richard; KIRBY, Robert; ROGERS, Marc; SUTTON, Kathy; WO2014/32801; (2014); A1;,
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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 36865-41-5 as follows. Quality Control of 1-Bromo-3-methoxypropane

A solution of PPh3 (42.8 g, 163.2 mmol) and 1-bromo-3-methoxypropane (25 g, 163.3 mmol) in toluene (70 mL) is heated at 150C in an autoclave for 44 h. After completion of the reaction, the mixture is filtered and the precipitate washed with toluene and dried under high vacuum for 4 h affording the title compound as a white powder: Rt (HPLC, Nucleosil C18, 10: 90-100: 0 CH3CN/H20 + 0. 1 % TFA within 5 min, then 100% CH3CN + 0. 1% TFA): 5.06 min.

According to the analysis of related databases, 36865-41-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/51911; (2005); A1;,
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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. 6358-77-6, name is 5-Bromo-2-methoxyaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8BrNO

5-(Dimethylphosphoryl)-2-methoxyaniline (0456) To a solution of 5-bromo-2-methoxyaniline (0.404 g, 2.00 mmol) in 8 mL DMF was added dimethylphosphine oxide (0.171 g, 2.20 mmol), palladium acetate (22.4 mg, 0.0100 mmol), XANTPHOS (69.4 mg, 0.120 mmol), and potassium phosphate (0.467 g, 2.20 mmol). The mixture was purged with nitrogen, and subjected to microwaves at 150 C. for 20 minutes. The reaction mixture was concentrated and purified by silica gel chromatography (0-20% 7N ammonia in methanol:dichloromethane) to afford the desired product (0.365 g, 85% yield).

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; Wang, Yihan; Huang, Wei-Sheng; Liu, Shuangying; Shakespeare, William C.; Thomas, Ranny M.; Qi, Jiwei; Li, Feng; Zhu, Xiaotian; Kohlmann, Anna; Dalgarno, David C.; Romero, Jan Antoinette C.; Zou, Dong; US2015/225436; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 207226-31-1, name is 1,3-Dibromo-5-(trifluoromethoxy)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 207226-31-1, SDS of cas: 207226-31-1

Dibromide D-l-2a (3.0 g, 9.38 mmol), sodium-tert-butoxide (1.26 mg, 13.13 mmol), BINAP (584 mg, 0.938 mmol) and tris-(dibenzylideneacetone)-palladium (85.9 mg, 0.094 mmol) are suspended in 60 mL toluene, combined with benzophenonimine (2.04 g, 11.25 mmol), and refluxed under an argon atmosphere for 3 d. Then the reaction mixture is filtered and the solvent is eliminated by distillation.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-5-(trifluoromethoxy)benzene, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/3999; (2009); A2;,
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Synthetic Route of 707-07-3,Some common heterocyclic compound, 707-07-3, name is (Trimethoxymethyl)benzene, molecular formula is C10H14O3, 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.

General procedure: To a stirred solution of the respective N-carbamate-protected aminovicinal diol 4 (0.50 mmol, 1 equiv) in CH2Cl2 (10 mL, 0.05 M) were added BF3·OEt2 (50 muL, 0.050 mmol, 0.1 equiv, 1.0 M solution in CH2Cl2) and trimethyl orthobenzoate (0.13 mL, 0.75 mmol, 1.5 equiv) at r.t. The resulting mixture was refluxed or stirred at r.t. under N2 until TLC showed complete conversion of the substrate. The reaction was quenched with sat. aq NaHCO3 and extracted with EtOAc (2 ×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (hexane/EtOAc) to give the desired product 5.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Trimethoxymethyl)benzene, its application will become more common.

Reference:
Article; Park, Heemin; Kwon, Yongseok; Shin, Jae Eui; Kim, Woo-Jung; Hwang, Soonho; Lee, Seokwoo; Kim, Sanghee; Synthesis; vol. 49; 12; (2017); p. 2761 – 2767;,
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Electric Literature of 53087-13-1,Some common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, molecular formula is C13H11BrO, 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 4 1-(3,4,5,6-Tetramethoxy-2-methylphenyl)-1-(3- benzyloxyphenyl) methanol An anhydrous tetrahydrofuran (50 ml) solution of 3,4,5,6-tetramethoxy-2-methylbenzaldehyde (14 g, 0.058 mol) was added dropwise under ice cooling to a Grignard reagent (150 ml tetrahydrofuran solution) prepared from 3-(benzyloxy)bromobenzene (18.4 g, 0.070 mol) and magnesium (1.87 g, 0.077 mol), and the resulting solution was stirred for 2 hours. The reaction solution was poured in an aqueous solution of saturated ammonium chloride and extracted with ether. The extract was washed with saturated brine and then dried. The reaction solution was filtered, the filtrate was concentrated and the obtained crude product was purified by silica gel column chromatography (hexane: ethyl acetate = 4:1) to obtain the titled compound (23.5 g, 0.055 mol, 95%).

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Suntory Pharma Co., Ltd.; Daiichi Suntory Biomedical Research Limited; EP1314712; (2003); A1;,
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Application of 7664-66-6, A common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, 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 mixture of 1-(4-chlorobenzyl)-3-(ethoxycarbonylmethyl)-6-iodoquinazoline-2,4-dion (200 mg, 0.4 mmol), palladium acetate (13.5 mg, 0.06 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (52.2 mg, 0.09 mmol), cesium carbonate (261 mg, 0.8 mmol) and dioxane (4 mL) was added 4-isopropoxyaniline (0.071 mL, 0.48 mmol) under nitrogen atmosphere, and the resulting mixture was heated at reflux for 2 hours. The reaction mixture was poured into a mixture of water (100 mL) and 5% aqueous citric acid (10 mL), and the resulting mixture was extracted with ethyl acetate (100 mL). The extract was washed by water (100 mL), dried over anhydrous sodium sulphate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the residue was precipitated by hexane to give 1-(4-chlorobenzyl)-3-(ethoxycarbonylmethyl)-6-(4-isopropoxyphenylamino)-quinazolin e-2,4-dion (7.7 mg, Yield: 3.7%) as yellow solid. 1H-NMR (delta ppm TMS/CDCl3): 1.28 (3H, t, J=7.2 Hz), 1.33 (6H, d, J=6.0 Hz), 4.24 (2H, q, J=7.2 Hz), 4.74 (1H, m), 4.88 (2H, s), 5.29 (2H, s), 5.61 (1H, s), 6.84 (2H, d, J=8.7 Hz), 6.91 (1H, d, J=9.0 Hz), 7.01 (2H, d, J=8.7 Hz), 7.11 (1H, dd, J=3.0, 9.0 Hz), 7.19 (2H, d, J=8.7 Hz), 7.30 (2H, d, J=8.7 Hz), 7.68 (1H, d, J=2.7 Hz).

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; Shionogi & Co., Ltd.; KAI, Hiroyuki; ENDOH, Takeshi; JIKIHARA, Sae; ASAHI, Kentaro; HORIGUCHI, Tohru; EP2604260; (2013); A1;,
Ether – Wikipedia,
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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. 175278-09-8, name is 4-Bromo-2-(trifluoromethoxy)aniline, A new synthetic method of this compound is introduced below., Computed Properties of C7H5BrF3NO

To a mixture of 4-bromo-2-(trifluoromethoxy)aniline (1024 mg, 4 mmol), isobutylboronic acid (612 mg, 6 mmol), caesium carbonate (612 mg, 6 mmol) and toluene/water (10:1, 10 mL) in a microwave tube was added Pd(dppf)Cl2 (146 mg, 5% eq) under argon atmosphere. The reaction mixture was reacted at 120? for 1 hour under microwave. After completion of the reaction, the mixture was filtered through Celite and washed with dichloromethane. The organic layer was concentrated in vacuo, and the residue was purified by a silica gel column to give 4-isobutyl-2-(trifluoromethoxy)aniline (662.8 mg), with a yield of 67.2%. MS (ESI) m/z: 255.9 (M+1).

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; Fudan University; WANG, Yonghui; HUANG, Yafei; QIU, Ruomeng; TANG, Ting; (68 pag.)EP3581561; (2019); A1;,
Ether – Wikipedia,
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These common heterocyclic compound, 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, 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. Computed Properties of C7H5BrF3NO

General procedure: A solution of substituted anilines (12.4 mmol) dissolved in 30 mL anhydrous THF was added very slowly into a stirred solution of triphosgene (1.40 g, 4.80 mmol) in 20 mL of THF. After stirringfor 15 min, triethylamine (2.90 mL, 20.6 mmol) was then added slowly to the reaction mixture. Stirring was continued for 20 min, various aromatic heterocyclic amines (12.0 mmol) in anhydrous THF (20 mL) was added directly to the above residue. After completion of the action, the reaction was quenched with dilute NaHCO3 and the solvent was subsequently removed in vacuo and extracted with ethyl acetate (3 30 mL). The organic layer was washed with water and brine, and dried over Na2SO4. After filtration and concentration in vacuo, the residues was purified by silicagel flash chromatography (PE/AcOEt = 5:1) gave as white solid (3a-3h) (yield: 30-50%).

The synthetic route of 5-Bromo-2-(trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shan, Yuanyuan; Wang, Chen; Zhang, Lin; Wang, Jinfeng; Wang, Maoyi; Dong, Yalin; Bioorganic and Medicinal Chemistry; vol. 24; 4; (2016); p. 750 – 758;,
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