Tag: M.W=100-200

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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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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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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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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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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Synthetic Route of 592-55-2, 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 592-55-2 as follows.

To a stirred solution of pentane 1,5-diol 1 (11 g, 105.76 mmol) in N,N-dimethyl formamide (30 mL) was treated with 60 % of NaH (4.5 g, 116.34 mmol) at 0 C and stirred at room temperature for 30 min.1-bromo-2-ethoxyethane 2 (12 mL, 105.76 mmol) in N, N- dimethyl formamide (20 mL) was added to the above reaction mixture at 0 C and stirred at room temperature and stirred for 16 h under argon atmosphere. The reaction mixture was quenched with ice water (200 mL) and extracted with ethyl acetate (3 x 250 mL). Combined organic layers were washed with brine (2 x 100 mL) and dried over Na2SO4, evaporated under reduced pressure. Crude residue was purified by column chromatography (100-200 silica gel) using 30 % ethyl acetate in hexanes to afford 5-(2-ethoxyethoxy) pentan-1ol 3 (5.1 g, 28.97 mmol, 27 % yield) as an oily liquid. TLC system: 70 % ethyl acetate in hexanes – Rf: 0.50; LCMS: m/z = 199.12 (M+Na) +

According to the analysis of related databases, 592-55-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; COCRYSTAL PHARMA, INC.; JACOBSON, Irina, C.; LEE, Sam SK; FEESE, Michael, David; (206 pag.)WO2020/23813; (2020); 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. 5961-59-1, name is 4-Methoxy-N-methylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 5961-59-1

Example 1: Key Intermediate (S)-N-(1-(4-methoxyphenyl)(methyl)amino)-1-carbonyl-3-phenyl-2-yl)propynamide (4 Preparation of The starting material Boc-L-phenylalanine (1) (8.75 mmol, 2.3 g) was added to 15 mL of anhydrous dichloromethane solution. To this solution was then added 1H-benzotriazol-1-yloxytripyrrolidinylhexafluorophosphate (10.9 mmol, 5.7 g). After stirring for 0.5 h under ice bath, N,N-diisopropylethylamine (21.87 mmol, 3.61 mL) and N-methyl-4-aminoanisole (7.29 mmol, 1.0 g) were added to remove the ice bath. Stir at room temperature for 12 h. After the reaction is completed, the solvent is distilled off under reduced pressure, then saturated sodium bicarbonate solution is added to the bottle residue, and ethyl acetate is extracted; the organic layer is separated, 1N HCl solution is added, and ethyl acetate is extracted; the organic layers are combined and saturated. The brine was washed and the organic phase was dried over anhydrous sodium sulfate; Filtration and evaporation of the solvent under reduced pressure gave the intermediate compound tert-butyl-(S)-(1-((4-methoxyphenyl)(methyl)amino)-1-oxo-3-phenylpropyl- 2-Carboxylic acid (2) Crude 2.63 g, yellow oil, 94% yield,

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; Shandong University; Zhan Peng; Wu Gaoshan; Liu Xinyong; Li Guoxiong; Kang Dongwei; Yu Ji; Sun Lin; (25 pag.)CN108033952; (2018); A;,
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Related Products of 104-92-7, 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. 104-92-7 name is 1-Bromo-4-methoxybenzene, 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.

General procedure: n-BuLi (1.2 mmol) was added to a THF (6 ml) solution ofaryl bromide (1 mmol) at -78C. After stirring for 1 h at same temperature, a THF solution of MOM-Cl or BOM-Cl (1.1 mmolin 4 ml dry THF) was added dropwise to it. Stirring was continuedfor another 1 h at same temperature and slowlywarmed to 0C over another 1 h and quenched with saturatedaqueous ammonium chloride solution. The organic layerwas separated and aqueous layer was extracted with diethylether. The combined organic layer was dried (Na2SO4) andevaporated. Column chromatographic purification gave thedesired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Article; Panda, Biswajit; Journal of the Indian Chemical Society; vol. 95; 8; (2018); p. 981 – 985;,
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Application of 651734-54-2, 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 651734-54-2 as follows.

Pd2dba3 (224mg; 0.245 mmol) and BINAP (305 mg; 0.49 mmol) was added to a solution of intermediate 25 (2g; 4.9 mmol), 2,6-difluoro-3,5-dimethoxyaniline (1.39g; 7.35 mmol) and Cs2003 (4.79g; 14.69 mmol) in dioxane (60 mL). The reaction mixture was heated overnight at 80C. Then, it was poured onto cooled water and the aqueous layer was extracted with DCM. The organic layer was dried over MgSO4, filtered and the solvent was evaporated. The resulting residue was cristallized from DIPE to afford 1.90g of intermediate 26 (75%).MP = 2600C (Kofler)

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; ASTEX THERAPEUTICS LIMITED; ANGIBAUD, Patrick Rene; QUEROLLE, Olivier Alexis Georges; PILATTE, Isabelle Noelle Constance; MEERPOEL, Lieven; PONCELET, Virginie Sophie; WO2014/174307; (2014); A1;,
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Related Products of 171290-52-1, A common heterocyclic compound, 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, molecular formula is C10H10O2, 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.

General procedure: Azide 13 (300 mumol), alkyne (750 mumol), CuSO4 (9.6 mg, 60 mumol) and sodium ascorbate (60.0 mg, 300 mumol) were dissolved in 1:1 t-BuOH/H2O (3 mL). The mixture was stirred for 2 h at rt. After the completion of the reaction, the mixture was filtered and washed with H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 * 70 mL). The combined organic extracts were dried over anhyd MgSO4, filtered, and concentrated by rotary evaporation (residue B). The solid A and residue B were combined and purified by column chromatography to afford 8 or 9.

The synthetic route of 171290-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Doohee; Park, Yunjeong; Yoon, Jieun; Aman, Waqar; Hah, Jung-Mi; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4855 – 4866;,
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