Month: July 2021

Reference of 24878-25-9, These common heterocyclic compound, 24878-25-9, name is 2,2′-Oxydianiline, 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.

L. Nicotinic acid acyl azide and bis(2-aminophenyl) ether were synthesized according to previous literatures [24-26], respectively. A solution of nicotinic acid acyl azide (1.04?g, 7.0?mmol) in toluene (30?mL) was refluxed under nitrogen for 1.5?h, and bis(2-aminophenyl) ether (0.60?g, 3.0?mmol) in acetonitrile (30?mL) was added dropwise. The mixture was stirred for another 1.5?h and cooled to room temperature. The precipitate that formed was collected by filtration and purified by recrystallization from CH3OH/DMF(V: V?=?2:1) to give a white solid. Yield: 1.07?g, 81%; mp: 285???286?C. 1H NMR (DMSO-d6, 400?MHz): delta 6.84 (d, 2H, J?=?7.6?Hz, Ar-H), 7.02 (t, 2H, J?=?5.2?Hz, Ar-H), 7.18 (t, 2H, J?=?5.6?Hz, Ar-H), 7.36 (dd, 2H, J?=?2.8?Hz, Ar-H), 7.99 (m, 2H, Py-H), 8.23 (d, J?=?2.8?Hz, 2H, Py-H), 8.35 (d, J?=?6.8?Hz, 2H, Py-H), 8.61 (s, 2H, Py-H), 8.75 (s, 2H, CONH), 9.52 (s, 2H, CONH). 13C NMR (DMSO-d6, 400?MHz): delta 152.98, 145.76, 143.53, 140.33, 136.81, 131.60, 125.47, 124.64, 124.15, 123.20, 120.23, 118.38. Anal. Calcd(%) for C24H20N6O3: C 65.45, H 4.58, N 19.08; found(%): C 65.49, H 4.62, N 19.03. FT-IR (KBr pellet, nu/cm-1): 3344 (m, NH), 1715 (s, CO), 1599 (s, NH). ESI-MS: m/z?=?441 [M+H]+, 463 [M+Na]+.

The synthetic route of 24878-25-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Chao; Yi, Xian-Mei; Chen, Dong-Mei; Zhu, Bi-Xue; Inorganica Chimica Acta; vol. 476; (2018); p. 123 – 128;,
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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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 1-Bromo-2-(2-methoxyethoxy)ethane

Example 9. 6-{4-[4-(5-Chloro-1H-indole-2-sulphonyl)-piperazine-1-carbonyl]-phenyl}-2-[2-(2-methoxv-ethoxv)-ethvll-2H-pvridazin-3-one. 6- [4- ( {4- [ (5-Chloro-lH-indol-2-yl) sulphonyl] piperazin-1-yl} carbonyl) phenyl]- pyridazin-3-ol (see WO 99/57113,0. 054 gram, 0.11 mmol), 0. 016 gram of anhydrous potassium carbonate (0.11 mmol, 1.0 eq. ) and 0.02 gram of 1-bromo-2-(2-methoxy- ethoxy) ethane (0.11 mmol, 1.0 eq. ) were mixed in 1.5 mL of dry N, N-dimethylformamide. The mixture was treated with microwave at 150 C for 1 hour. Without any work-up, purification was performed on preparative HPLC, which gave 0.023 gram of 6-{4-[4-(5-chloro-1H-indole-2-sulphonyl)-piperazine-1-carbonyl]-phenyl}-2-[2-(2- methoxy-ethoxy)-ethyl]-2H-pyridazin-3-one (yield 36 %).

The synthetic route of 54149-17-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2005/65688; (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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., Application In Synthesis of (2,4-Dimethoxyphenyl)methanamine

Step 1: N-(2,4-dimethoxybenzyl)-4-iodo-5-methylpyridin-2-amine A solution of 2-fluoro-4-iodo-5-methylpyridine (85 g, 340 mmol) in 1-(2,4-dimethoxyphenyl)methanamine (270 mL, 1.68 mol) was allowed to stir at 110 C. overnight. The reaction mixture was allowed to cool to rt and diluted with EtOAc. A precipitate formed and was filtered and then washed with EtOAc. The solid was purified further by column chromatography to give N-(2,4-dimethoxybenzyl)-4-iodo-5-methylpyridin-2-amine (138 g, 50%).

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; MILLENNIUM PHARMACEUTICALS, INC.; Chau, Ryan W.; Cullis, Courtney A.; Duffey, Matthew O.; Gipson, Krista E.; Hu, Yongbo; Li, Gang; Sintchak, Michael D.; Vos, Tricia J.; US2013/165464; (2013); A1;,
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Related Products of 41789-95-1, 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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In a typical reaction, the Wang resin (3, 2.0 g, 1.2 mmol/g, 100-200 mesh and 1% DVB) was swollen in CH2Cl2 (20 mL). 5-Bromopentanoic acid (4, 2.15 g, 12.0 mmol) and DIC (1.51 g, 12.0 mmol) were dissolved in the minimum volume of CH2Cl2/DMF (1:1) required for complete dissolution. The activated scaffold solution was added to the resin, followed by the addition of slurry of DMAP (4 mg, 10 mol %) in CH2Cl2 (0.5 mL). The reaction vessel was shaken at room temperature for 48 h. The resin was washed with CH2Cl2 (2 × 25 mL), DMF (2 × 25 mL), MeOH (2 × 25 mL) again followed by DMF (2 × 25 mL), CH2Cl2 (3 × 25 mL), and then further dried in vacuo overnight to afford the resin-bound 5-bromopentanoic acid in good yield (2.73 g, 81%). Next, to the resin-bound 5-bromopentanoic acid (2.70 g, 3.9 mmol), swelled in DMF (10 mL), K2CO3 (2.13 g, 15.6 mmol) was added at ambient temperature, and the reaction suspension was stirred for another 30 min. Later, methyl 2-azido-4-hydroxy-5-methoxybenzoate (5, 1.73 g, 7.8 mmol) was added to the resin. The reaction suspension was stirred at 50 C for 48 h. The solid-support was washed with water (3 × 20 mL), CH2Cl2 (2 × 20 mL), MeOH (3 × 15 mL), and then dried in vacuo to afford the resin-bound precursor 6a (3.07 g, 75%). To a suspension of this resin-bound ester in 1,4-dioxane (10 mL) was added 1 N NaOH solution (2.5 mL) and the reaction mixture was heated at 80 C for 12 h. On cooling, the resin was filtered and rinsed with water (2 × 15 mL), water/dioxane (1:9, 2 × 15 mL), MeOH (2 × 15 mL), CH2Cl2 (2 × 15 mL), Et2O (2 × 15 mL) and dried in vacuo to afford the resin-bound acid. Next, to the resin-bound 2-azido-4-(5-ethoxy-5-oxopentyloxy)-benzoic acid (2.81 g, 2.6 mmol) swelled in CH2Cl2 (10 mL), EDCI (0.99 g, 5.2 mmol), HOBt (0.71 g, 5.2 mmol) and l-proline methyl ester (7a, 0.84 g, 6.5 mmol) were added. This reaction mixture was stirred for 12 h at room temperature, then resin was filtered and washed with H2O (3 × 10 mL), CH2Cl2 (2 × 10 mL), MeOH (3 × 10 mL) and Et2O (3 × 10 mL) to afford the resin bound methyl 5-(5-azido-4-(2-formylpyrrolidine-1-carbonyl)-2-methoxyphenoxy) pentanoate 8a in good yield (2.89 g, 71%). To a suspension of this resin (0.110 g, 1.2 mmol) in CH2Cl2 (5 mL), AlCl3 (0.79 g, 6 mmol), NaI (0.22 g, 2 mmol) and 2-(4-methoxyphenyl)ethanamine (9a, 0.35 mL, 2.4 mmol) were added at room temperature and stirred for 6 h. Aqueous 1 M potassium carbonate solution (2 mL) was added to the reaction mixture followed by excess of NaI, quenched with saturated sodium thiosulfate (Na2S2O3), and then resin was separated by simple filtration and washed with CH2Cl2 (10 mL). The removal of excess amine impurities from the final resin cleaved crude product was achieved by solid-supported liquid-liquid extraction (SLE) with a fritted vessel previously packed with ?Varian?s Hydromatrix?. The crude compound 1a which contains excess of amine was passed through the Hydromatrix support into a collection plate below, while the amine salts were retained by the solid matrix, resulting in the effective removal of the amine impurities. This filtrate and washings were evaporated to dryness under reduced pressure. Finally, it was further purified by the preparative thin layer chromatography by using ethyl acetate:methanol (98:2) as eluent to afford the corresponding compound 1a in high purity (brown solid, 0.013 g, 56%).

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

Reference:
Article; Kamal, Ahmed; Prabhakar; Shankaraiah, Nagula; Markandeya, Nagula; Venkat Reddy; Srinivasulu, Vunnam; Sathish, Manda; Tetrahedron Letters; vol. 54; 33; (2013); p. 4435 – 4441;,
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Reference of 645-36-3, 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 645-36-3 as follows.

General procedure: The aromatic aldehyde or ketone and aminoacetaldehyde diethyl acetal were placed in a 500 mL round-bottom flask and toluene was added (see conditions in table 1 b). The mixture was heated under reflux in a Dean-Stark apparatus (around 4 h, see conditions in table 1 b) until complete separation of water was achieved. Toluene was then evaporated to give after drying the desired iminoacetal in almost quantitative yield. The iminoacetal ANP 31058A was prepared from 3,4-dimethoxybenzylamine (23.2 mmol) and pyruvic aldehyde dimethyl acetal (35.5 mmol) using the same general procedure (see conditions in table 1 b).

According to the analysis of related databases, 645-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALLERGAN, INC.; EXONHIT THERAPEUTICS SA; LEBLOND, Bertrand; BEAUSOLEIL, Eric; CASAGRANDE, Anne-Sophie; DESIRE, Laurent J.R.; PANDO, Matthew P.; DONELLO, John E.; YANG, Rong; TAVERNE, Thierry; CHAUVIGNAC, Cedric; WO2014/71044; (2014); A1;,
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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. 20012-63-9, name is 2-(Benzyloxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 20012-63-9

Step L: N-Trifluoroacetyl 2-Benzyloxyaniline (25) To a stirred, near solution of amine (24) (5.0 mM) in dry diethyl ether (30 mL) is added anhydrous sodium carbonate (6.0g., 57 mM) and the resultant mixture cooled in an ice-water bath. Trifluoroacetic anhydride (1.5 mL, 10.6 mM) is added dropwise to this cold mixture over 2 minutes, the color changing to a yellowish red. After 2 hours the cooling-bath is removed and the mixture allowed to stir at ambient temperatures overnight. After filtering, the filtrate is concentrated in vacuo and then pumped to yield 1.3 g. of the title compound (25) as a pale tan (with some reddish-brown color around the edges) crust.

The synthetic route of 20012-63-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO. INC.; EP526093; (1993); A1;,
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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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Bromo-2-(2-bromoethoxy)ethane

a) Sodium hydroxide (50% w/w) (20.04 ml, 379.60 mmol) was added to (3R)-4-(2-chloro-6-(methylsulfinylmethyl)pyrimidin-4-yl)-3-methylmorpholine (2.2 g, 7.59 mmol), 1-bromo-2-(2-bromoethoxy)ethane (3.79 ml, 30.37 mmol) and tetraoctylammonium bromide (0.415 g, 0.76 mmol) in methyl THF (20.05 ml). The resulting mixture was stirred at RT for 90 minutes. The reaction mixture was diluted with methyl THF (50 mL), and washed sequentially with water (50 ml) and saturated brine (5 ml). The organic layer was dried over MgSO4, filtered and then evaporated onto silica (30 g). The resulting powder was purified by flash chromatography on silica, eluting with a gradient of 0 to 5% MeOH in DCM. Pure fractions were evaporated to afford (3R)-4-(2-chloro-6-(4-(methylsulfinyl)tetrahydro-2H-pyran-4-yl)pyrimidin-4-yl)-3-methylmorpholine (1.360 g, 50%); 1H NMR (400 MHz, DMSO-d6) 1.84-1.96 (1H, m), 2.02 (1H, td), 2.09 (3H, d), 2.27-2.45 (2H, m), 3.14 (1H, d), 3.10-3.26 (3H, m), 3.24 (1H, d), 3.33-3.41 (1H, m), 3.45 (1H, td), 3.60 (1H, dd), 3.71 (1H, d), 3.78-3.87 (1H, m), 3.87-3.97 (2H, m), 4.07 (1H, d), 4.32-4.48 (1H, m), 6.76 (1H, s); m/z: (ES+) MH+, 360.11 and 362.06.

According to the analysis of related databases, 5414-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; US2011/306613; (2011); A1;,
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These common heterocyclic compound, 104197-14-0, name is 4-Bromo-2,6-difluoroanisole, 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. SDS of cas: 104197-14-0

To a solution of compound 5.2 (0.15 mL,1.22 mmol) in DME (7 mL) was added tetrakis triphenylphosphine palladium (78 mg,0.067 mmol). Stirring was continued at r.t. 5 min. 2-formyl phenyl boronic acid 5.1 (202 mg,1.35 mmol) and K2CO3 (745 mg,3.56 mmol) were added in turn. Stirring was continued at reflux 4h. The solvent was removed in vacuo. The crude was taken up with water and extracted with EtOAc (3 x 20 ml). The organic phase was washed with brine and dried over Na2S04. Flash chromatography purification (eluent PET/EtOAc) of the reaction crude afforded the title compound 5.3 (180 mg,0.72 mmol) as brownish oil.lH NMR (200 MHz,CDCI3) delta 4.20 (s,3H), 6.95 (d, / = 6.7 Hz,2H), 7.40 (d, / = 7.7 Hz,2H), 7.53 (d, / = 8.6 Hz,1H), 7.64-7.70 (m,1H), 8.03 (d, / = 7.8 Hz,1H), 10.02 (s,1H).

The synthetic route of 4-Bromo-2,6-difluoroanisole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TES PHARMA S.R.L.; PELLICCIARI, Roberto; (253 pag.)WO2018/69532; (2018); 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. 82830-49-7, name is 2-Fluoro-1,4-dimethoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Fluoro-1,4-dimethoxybenzene

EXAMPLE THREE: Synthesis of Ligand 6; An oven-dried three-neck 100 rnL round bottom flask, which was equipped with a magnetic stir bar and charged with Magnesium shavings (360 mg, 15.36 mmol), was fitted with a reflux condenser, glass stopper, and rubber septum. The flask was evacuated and backfilled with argon (this process was repeated a total of 3 times) and then THF (40 mL) and 2,4,6-triisopropylbromobenzene (3.62 g, 12.8 mmol) were added via syringe. The reaction was heated to reflux and 1 ,2-dibromethane (40 muL) was added dropwise. The reaction was allowed to stir at reflux for 1 h and then was cooled to room temperature. A separate oven-dried 500 mL round bottom schlenk flask, which was equipped with a magnetic stir bar and fitted with a septum, was evacuated and backfilled with argon (this process was repeated a total of 3 times) and then THF (160 mL) and 1 ,4-dimethoxy-2- fluorobenzene (2 g, 12.8 mmol) were added to the flask via syringe. The reaction was cooled to -78 0C and n-BuLi (2.5 M in Hexane, 5.12 mL, 12.8 mmol) was added dropwise over a 15 min period. The solution was stirred for 30 min and the Grignard reagent, which was prepared in the first reaction vessel, was added via cannula transfer over a 20 min period and allowed to stir at -78 0C for 1 h. The reaction was warmed to room temperature slowly where it was stirred for an additional 3 h. Under a constant flow of argon the septum was removed and anhydrous CuCl (1.267 g, 12.8 mmol) was added quickly. The ClP(t-Bu)2 (2.44 mL, 12.8 mmol) was then added via syringe and the schlenk tube was sealed with a Teflon screw cap. The reaction was heated to 75 0C for 48 h and then cooled to room temperature. The reaction was quenched with 30% aqueous NH4OH (100 mL) and the resulting suspension was extracted with EtOAc (200 mL). The organic layer was washed with 30% aqueous NH4OH (3 x 100 mL) and brine (100 mL), dried over MgSO4, filtered, and concentrated on a rotary evaporator to yield a thick yellow oil. The crude material was taken up in minimum amount of hot MeOH and placed in a -25 0C freezer over night to yield 1.11 g (18%) of white crystals.

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; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; WO2009/76622; (2009); A2;,
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Related Products of 5414-19-7, These common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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.

Into a 1000-mL round -bottom flask was placed a solution of 4-(benzyloxy)phenol (5 g, 24.97 mmol, 1.00 equiv) in tetrahydrofuran (200 mL), 37 %NaOH (200 mL), and l-bromo-2- (2-bromoethoxy)ethane (57.5 g, 247.94 mmol, 10.00 equiv). The resulting solution was stirred overnight at 70 C in an oil bath. The reaction mixture was cooled. The resulting solution was extracted with dichloromethane and the organic layers were combined. The solution was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel column (ethyl acetate/petroleum ether) to afford l-(benzyloxy)-4-[2-(2- bromoethoxy)ethoxy]benzene (6.67g, 76%) as a white solid. LC/MS (ESI) m/z: 350.05 [M+1] +.

The synthetic route of 5414-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARVINAS, INC.; QIAN, Yimin; CREW, Andrew, P.; CREWS, Craig, M.; DONG, Hanqing; HORNBERGER, Keith, R.; WANG, Jing; (606 pag.)WO2018/140809; (2018); A1;,
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