Tag: M.W=200-300

17061-62-0, name is Bis(4-methoxybenzyl)amine, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 17061-62-0

To a stirred solution of 100.1 (100 g, 0.39 mol) in DCM (1 L) was added TEA (71 mL, 0.51 mol), followed by dropwise addition of methanesulfonyl chloride (36 mL, 0.47 mol). The internal temperature was kept between 5-10 C during the addition of methane sulfonyl chloride. Once the addition was complete, the cooling bath was removed and the mixture was stirred at RT until TLC analysis indicated that the reaction was complete. Thereafter, water (1 L) was added, the layers were separated and the aqueous layer was extracted with DCM (2 x 500 mL). The combined organic layers were washed with brine (2 x 1 L), dried over Na2SO4, and concentrated in vacuo. The residue was purified on a silica gel column, employing a gradient of 10-80% EtOAc in hexanes, to afford 120 g (0.36 mol, 92%) of 101.0 as white solid.1H-NMR (400 MHz, CDCl3) delta 7.26 (dd, J=2.12, 6.60 Hz, 4H) 6.91 (dd, J=2.12, 6.62 Hz, 4H) 4.28 (s, 4H) 3.83 (s, 6H) 2.75 (s, 3H).

The synthetic route of 17061-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; KREIMAN, Charles; (308 pag.)WO2018/93579; (2018); A1;,
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Application of 36805-97-7, 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. 36805-97-7 name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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 10 2′-(6-Carbamimidoyl-1-methyl-1H-indol-3-ylmethyl)-4-methoxy-5′-methylcarbamoyl-biphenyl-2-carboxylic acid; Part A. 3-bromo-4-formyl-benzoic acid tert-butyl ester:; A solution of 3-bromo-4-methylbenzoic acid (5 g, 0.023 mol) in 40 mL toluene was heated to 80 C. in an oil bath and DMF-di-t-butylacetal (22.4 ml, 0.093 mol) was added dropwise over 20 min. The resulting mixture was heated for an additional 1 h and then cooled to rt and evaporated to dryness. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the t-butyl ester (5.1 g, 81%) which was dissolved in 50 mL CCl4 and treated with N-bromosuccinimide (6.7 g, 0.037 mol) and benzoylperoxide (0.22 g, 0.94 mmol). The mixture was then heated in an 80 C. oil bath overnight. Solvent was removed by evaporation, and residue was taken up in EtOAc and washed with water, sat’d Na2CO3 and brine then dried over anh. Na2SO4, filtered and concentrated. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the dibromide (7.5 g, 94%) to which was added 30 mL morpholine and the mixture was heated overnight at 60 C. After cooling to rt, the mixture was diluted with EtOAc and washed with 5% citric acid solution until aqueous phase stays at pH 4, then with sat’d bicarbonate solution and brine. Organic phase was dried and concentrated to provide the aldehyde in 74% yield after flash chromatography. 1NMR (500 MHz, CDCl3) delta 10.40 (s, 1H); 8.24 (s, 1H); 7.95 (m, 1H); 7.93 (m, 1H); 1.61 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, and friends who are interested can also refer to it.

Reference:
Patent; Smallheer, Joanne M.; Corte, James R.; US2005/228000; (2005); A1;,
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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. HPLC of Formula: C11H25NO2

(b) tert-Butyl1-(trifluoroacetyl)azetidine-3-carboxylate 1,1-di-tert-butoxy-N,N-dimethylmethanamine (16.5 g, 81 mmol) was added to a solution of 1-(trifluoroacetyl)azetidine-3-carboxylic acid (5 g, 25 mmol) and the mixture was heated to reflux for 8 hours. LC-MS showed remaining starting material and therefore an additional amount of 1,1-di-tert-butoxy-N,N-dimethylmethanamine (21.2 g, 81 mmol) was added and the heating was continued over night. LC-MS showed still some remaining starting material (starting material/product about 1/2) and the THF was exchanged for toluene (100 mL) and the mixture heated to 100 C. (oil bath temperature) for 2 hours. The solvent was evaporated and the residue dissolved in EtOAc (200 mL). The organic phase was washed with NaHCO3(sat) (2*50 mL), water (2*50 mL), Brine (50 mL), dried (Na2SO4), filtered and evaporated to give the desired product. Yield: 4.5 g (70%).

The synthetic route of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; US2008/171732; (2008); 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. 116557-46-1, name is 3-Bromo-2-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Bromo-2-methoxyaniline

Step 3[00174j IntlO (2.0 g, 9.9 mmol) was dissolved in dioxane (40 mL) and the vessel purged with nitrogen for 5 minutes. Next bis(pinacolato)diborone (3.77 g, 14.85 mmol), [1,1 ?-bis(diphenylphosphino)ferrocene] dichloropalladium (II) complex with dichloromethane (404 mg, 0.49 mmol) and potassium acetate (2.91 g, 29.7 mmol) were added. The flask was evacuated and backfilled with nitrogen, and then heated to 100 Cfor 15 hours. Water was added to quench the reaction and the product was then extracted with EtOAc. The combined organic layers were washed with brine (x3), dried over sodium sulfate, filtered, concentrated and purified using automated chromatography (elutes at 40% ethyl acetate) to provide Intl 1 (2.0 g, 8 1%). ?H NMR (400MHz, chloroform-d) oe 7.12 (dd,J=7.3, 1.8 Hz, 1H), 6.96-6.89 (m, 1H), 6.88-6.83 (m, 1H),3.82 (s, 3H), 1.37 (s, 12H). LC retention time 0.65 [J]. m/z: 250 (MHj.

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 116557-46-1.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; WEINSTEIN, David S.; WROBLESKI, Stephen T.; TOKARSKI, John S.; KUMAR, Amit; WO2014/74661; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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 36805-97-7, SDS of cas: 36805-97-7

A solution of (S)-(+)-Z-4-amino-2-hydroxybutyric acid (5) (5 g, 19.74 mmol) in toluene (38 mL) containing N,N-dimethylformamide di-tert-butyl acetal (18.92 mL, 78.96 mmol) was heated to 95C for 3 h. The solvent was then evaporated and the crude product was purified by flash chromatography on silica gel (n-hexane/EtOAc = 7:4) to give (6) (3.4 g, 55.7 % yields) as yellow solid. Mp 42-44C; [alpha]20D= – 5.9 (c= 10.1 mg/ml, CHCl3) 1H-NMR (CDCl3) delta: 1.47 (s, 9H); 1.76-1.85 (m, 1H); 1.94-2.09 (m, 1H); 2.74 (br s, 1H); 3.36 (dd, J= 6.04 Hz, J= 11.99 Hz, 2H); 4.10 (dd, J= 4.02 Hz, J= 8.05 Hz, 1H); 5.09 (s, 2H); 5.21 (br s, 1H); 7.31-7.37 (m, 5H) Anal. Calcd. for C16H23NO5: C, 62.12; H, 7.49; N, 4.53. Found: C, 62.22; H, 7.48; N, 4.53.

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; Bracco Imaging S.p.A; EP2149568; (2010); A1;,
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Reference of 17715-69-4, These common heterocyclic compound, 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, 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: A suspension of Pd2(dba)3 (6.9mg, 0.0075mmol), tBu3PHBF4 (8.7mg, 0.03mmol), KOH (42mg, 0.75mmol), aryl bromide 4 (0.36mmol) and tetralone 3 (0.3mmol) in a mixture of dioxane/water (4:1, v/v, 3mL) was degassed and heated under Ar and microwave irradiation (80W of initial power, 100°C, 40min, infrared probe). Then, the mixture was allowed to cool to rt, diluted in AcOEt, washed with saturated NH4Cl solution, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography. Dioxane quality is extremely important for the success of the reaction. Characterization of alpha-aryl-alpha-tetralones is given in Ref.[26].

Statistics shows that 1-Bromo-2,4-dimethoxybenzene is playing an increasingly important role. we look forward to future research findings about 17715-69-4.

Reference:
Article; Fernandes, Talita de A.; Costa, Paulo R. R.; Manvar, Dinesh; Basu, Amartya; Kaushik-Basu, Neerja; Domingos, Jorge L. O.; Nichols, Daniel Brian; European Journal of Medicinal Chemistry; vol. 112; (2016); p. 33 – 38;,
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Synthetic Route of 24988-36-1, 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 24988-36-1 as follows.

Into a 200-mL three-neck flask were put 7.1 g (24 mmol) of 1,5-dibromo-2,4-dimethoxybenzene, 2.8 g (20 mmol) of 2-fluorophenylboronic acid, 12 mL of toluene, 12 mL of diethylene glycol dimethyl ether, and 50 mL of a sodium carbonate aqueous solution (2 mol/L). This mixture was degassed by being stirred while the pressure in the flask was reduced. After the degassing, the atmosphere in the flask was replaced with nitrogen, and the mixture was heated to 80 C. To this mixture was added 0.55 g (0.48 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at the same temperature for 3 hours. After the mixture was cooled down to the room temperature, 4.5 g (32 mmol) of 2-fluorophenylboronic acid and 0.12 g (0.29 mmol) of 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl were added to the mixture and then the mixture was degassed under reduced pressure. After the degassing, the atmosphere in the flask was replaced with nitrogen, and the mixture was heated to 80 C. again. After that, 30 mg (0.13 mmol) of palladium(II) acetate was add ed to the mixture, and stirring was performed at the same temperature for 4 hours. After the stirring, the mixture was cooled down to the room temperature, and the mixture was separated into an organic layer and an aqueous layer. The obtained aqueous layer was subjected to extraction with toluene three times, the extracted solution and the organic layer were combined, and this mixture was washed with saturated saline and dried with anhydrous magnesium sulfate. The obtained mixture was gravity-filtered, and then the obtained filtrate was concentrated to give a brown oily substance. This oily substance was purified by silica gel column chromatography (a developing solvent was subjected to a gradient to change from hexane to chloroform gradually) to give 7.2 g (22 mmol) of a target pale yellow oily substance at a yield of 92%. A synthesis scheme of the above synthesis method is shown in (B-2) below.

According to the analysis of related databases, 24988-36-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; Kawakami, Sachiko; Ishiguro, Yoshimi; Takahashi, Tatsuyoshi; Hamada, Takao; Seo, Hiromi; Seo, Satoshi; (113 pag.)US9997725; (2018); B2;,
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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. 944317-92-4, name is 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene

Outside the glovebox, a 100 mL Schlenk flask equipped with a magnetic stir bar was charged with commercially available 3-(trifluoromethyl)benzoic acid (BFA) (3.09 g, 16.2 mmol) and bromoanisole BrMIP (3.60 g, 14.6 mmol). The flask was transferred to glovebox (%O2 ?0.005) and Pd(OAc)2 (157 mg, 5 mol %), n-butyl-di-1-adamantylphosphine (530 mg, 10 mol %), Cs2CO3 (11.92 g, 36.6 mmol) and powdered dry molecular sieves 3 A (1.0 g) were added. The flask was closed with the rubber septum and taken out of the glovebox. Anhydrous DMF degassed with nitrogen was added through the septum and the obtained mixture was first stirred at room temperature for 1 h under the positive pressure of nitrogen, and then placed in a preheated oil bath (145 C) for 24 h. The reaction mixture was cooled to room temperature and quenched with 2M HCl (100 mL). Ethylacetate (50 mL) was added and the resulting suspension was stirred for 15 min, filtered through a pad of celite and the layers were cut. The water layer was extracted with ethyl acetate (50 mL) and all organic phases were combined, washed with brine (50 mL) and evaporated under reduced pressure to obtain a yellow oil. The crude product was purified by column chromatography to give 4′-fluoro-5′-Isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carboxylic acid as a colorless oil (3.11g, 60%). 1H NMR (DMSO-d6) delta 0.95 (d, J = 8.0, 6H), 3.36 (s, 1H), 626 (d, J =12.0, 1H), 6.83 (d, J = 8.0, 1H), 7.03 (d, J = 8.0, 1H), 7.25 (m, 1H), 7.74 (s, 1H).

The synthetic route of 944317-92-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEK Pharmaceuticals d.d.; EP2468736; (2012); A1;,
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Application of 116557-46-1,Some common heterocyclic compound, 116557-46-1, name is 3-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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 mixture of 3-bromo-2-methoxyaniline (3 g), 3-carboxyphenylboronic acid (2.94 g), bis(triphenylphosphine)palladium(II)chloride [PdCl2(PPh3)2] (0.30 g) and potassium carbonate (5.2 g) in ethanol (100 mL) and water (20 mL) was heated to about reflux temperature and stirred for about 28 hours. The hot mixture was filtered to remove the catalyst. The clear filtrate was concentrated under vacuum. To the residue, water (50 mL) and methanol (50 mL) was added, acidified to pH 3-5 using hydrochloric acid and stirred for about 30 minutes at about room temperature. The slurry was filtered, washed with n-hexane (50 mL) and dried in an oven at about 55 C. to about 60 C. for about 12 hours. Yield: 1.8 g 1H NMR (300 MHz in DMSO-d6): delta 8.08 (s, 1H), 7.89-7.92 (d, 1H), 7.73-7.75 (d, 1H), 7.51-7.56 (t, 1H), 6.87-6.92 (t, 1H), 6.72-6.74 (d, 1H), 6.50-6.53 (d, 1H), 3.27 (s, 3H)

The synthetic route of 116557-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glenmark Generics Limited; Upadhye, Bhargav Krishnaji; Jagadale, Shivaji Eknath; Soni, Mukesh; US2015/87845; (2015); A1;,
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Electric Literature of 450-88-4, These common heterocyclic compound, 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, 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.

The solution of anisole of formula 2 (Scheme 6) (61 .5 g, 0.3 mol) in 1 ,2-dichloroethane (DCE) (600 mL) was cooled to -10 C and AICI3 was added in portions, maintaining the temperature below 2 C. The solution was then cooled to -5 C and acetyl chloride (56 mL, 0.79 mol) was added dropwise maintaining the internal temperature below 5 C. The reaction mixture was aged for 1 hour at 0 C. At this time HPLC showed no more starting material. The reaction mixture was quenched into ice (600 g) at a rate such that the internal temperature remained below 20 C. The resulting mixture was extracted with EtOAc (400 mL) and the organic phase then washed with 1 HCL (400 mL), saturated NaHC03 (400 mL) and brine (200 mL), dried over Na2S0 and filtered. The solvent was removed under reduced pressure to give acetophenon of formula 3 (Scheme 6) as a white solid (74.0 g, 100%): mp 1 13-1 17 C; H NMR (CDCI3) 5 2.59 (d, J = 5.1 Hz, 3H), 3.95 (s, 3H), 6.64 (d, J = 12.5 Hz, 1 H), 8.13 (d, J = 7.9 Hz, 1 H).

The synthetic route of 450-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2013/91696; (2013); A1;,
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