Author: Jessica.F

Application of 2216-69-5, A common heterocyclic compound, 2216-69-5, name is 1-Methoxynaphthalene, molecular formula is C11H10O, 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: 1-Methoxy-3,5-dimethylbenzene (100mg, 0.73 mmol), N-Bromosuccinimide (NBS,260 mg,1.46 mmol) and one ball (5 mmdiameter, stainless steel) were transferred to a milling jar (10 mL, stainlesssteel). The ball-milling operation was performed and the progress of reactionwas monitored by TLC/1H NMR.[1]After completion, the reaction mixture was transferred into 30 mL ethyl acetateand cooled at 0 C. The product was isolated as filtrate upon paper filtrationand waste succinimide as precipitate. The resulting filtrate were concentrated in vacuoto isolate 250 mg (yield: 85%) of 2bas colourless powder. To test the efficiency in largescale, the reaction was also performed for the mono-bromination of1-methoxy-3,5-dimethylbenzene in 1.3 g scale for 1 h and the product wasisolated in 87% yield.[1] Themilling apparatus was stopped and small portion of the sample was collectedfrom the reaction jar to study either TLC/ proton NMR. Following, the reaction was started again andthis operation time was excluded for reporting the reaction timing.

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:
Article; Bose, Anima; Mal, Prasenjit; Tetrahedron Letters; vol. 55; 13; (2015); p. 2154 – 2156;,
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Electric Literature of 5961-59-1,Some common heterocyclic compound, 5961-59-1, name is 4-Methoxy-N-methylaniline, molecular formula is C8H11NO, 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 synthesis of target compound 3 (Scheme 1C), started with the synthesis of a reported method for compound i.?3 2-Bromo-i,i-diethoxyethane (compound 10) was reacted with ethyl2-cyanoacetate to obtain compound 1 lwhich was cyclized to compound 12 using acetamidine hydrochloride under basic conditions. Chlorination of compound 12 using POC13 provided compound 13 in 80% yield. Displacement of the chloride of compound 13 with 4-methoxy-N- methyl aniline (compound 14) and catalytic amounts of HC1 in isopropanol, provided compound1. Methylation of compound 1 with Mel under basic conditions afforded compound 3 in 85% yield. The synthesis of target compound 5 (Scheme 1C), involved N-formylation of 4-methoxy- 2-methylanline (compound 15) to afford compound 16 in 70% yield. LAH reduction of compound 16 provided substituted aniline compound 17. Displacement of the chloride of compound 13 with anilines (compounds 15 and 17) and catalytic amounts of HC1 in isopropanol provided compounds 4 and 5 (75% and 70% respectively).

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

Reference:
Patent; DUQUESNE UNIVERSITY OF THE HOLY SPIRIT; GANGJEE, Aleem; (91 pag.)WO2016/22890; (2016); A1;,
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Synthetic Route of 41365-75-7,Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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.

Example 35; 3-(l-(((35,4/f)-l-(cyclopentanecarbonyl)-4-hydroxy-4-phenylpyrrolidin-3-yl)methyl)pi peridin-4-yl)-l-(4-(trifluoromethyl)benzyl)-3,4-dihydropyrimidiii-2(lH)-oneStep ACyclopentyl((3R,4S)-4-((4-(3,3-diethoxypropylamino)piperidin-l-yl)methyl)-3-hydroxy-3-p henylpyrrolidin-l-yl)methanone Following the procedure in Scheme 6, a mixture of l-(((3S,4R)-l-(cyclopentanecarbonyl) – 4-hydroxy-4-phenylpyrrolidin-3-yl)methyl)piperidin-4-one (1.0 g, 2.7 mmol), acetic acid (0.16 mL, 2.7 mmol), NaBH(OAc)3 (0.86 g, 4.05 mmol) and 3,3-diethoxypropan-l-amine (0.48 mL, 2.97 mmol) in diy THF (8 mL) was stirred at room temperature overnight. After this time, the mixture was diluted with EA and washed sequentially with NaOH, NaHCO3 and brine. The organic phase was dried over Na2SO4 and concentrated to yield crude amine which was used without further purification in the next step. MS (ESI, Pos. 1.5 kV) m/z 502.5 (M+H)+, 524.5 (M+Na)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Amino-3,3-diethoxypropane, its application will become more common.

Reference:
Patent; SHANGHAI TARGETDRUG CO., LTD.; AVEXA LIMITED; WO2009/89659; (2009); 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. 37466-89-0, name is 3-Methoxybenzene-1,2-diamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Methoxybenzene-1,2-diamine

Step 1: Reaction of 1,2-diamino compound (Chemical Formula 2) with oxalic acid; A 3-methoxybenzene-l,2-diamine compound (1.86 g, 13.5 mmol) represented by Chemical Formula 2-1 and oxalic acid (1.23 g, 13.6 mmol) were added to 10 mL of 3 N HCl solution. After stirring at room temperature for 10 minutes, reaction was carried out for 3 days under reflux. Then, after cooling to room temperature, the reaction mixture was filtered. The filtered compound was repeatedly washed with cold water to obtain a quinoxaline-2,3- dione compound (2.26 g, 87%) represented by Chemical Formula 3-1.1H NMR (500 MHz, DMS(Hi6) 3.86 (s, 3H), 6.75 (d, J = 8.1 Hz1 IH), 6.80 (d, J= 8.0 Hz, IH), 7.05 (t, J = 8.2 Hz, IH), 11.24 (br s, IH), 11.91 (br s, IH); n/z ( [M+l] ) 139.

The synthetic route of 37466-89-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; AMOREPACIFIC CORPORATION; WO2009/41789; (2009); A2;,
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Some common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, molecular formula is C6H15NO2, 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. Recommanded Product: Bis(2-methoxyethyl)amine

The product from step 27 1 (440 mg, 1.36 mmol) was dissolved in 7 DMF (25 mL), treated with HOBt.H2O (624 mg, 4.08 mmol), and 6 EDC.HCl (786 mg, 4.10 mmol) and stirred for 30 min at room temperature. 43 Bis(2-methoxylethyl)amine (620 mL, 559 mg, 4.20 mmol) was added and the resulting mixture was stirred at room temperature for 16 h and concentrated. The residue was partitioned with water and EtOAc. The EtOAc layer was separated and the aqueous was extracted again with EtOAc. The combined organic layers were washed with 0.5 N HCl, saturated sodium bicarbonate, and brine. The organic layer was dried (Na2SO4), filtered and concentrated to afford 214 mg of 44 3-(bis(2-methoxyethyl)amino)-6-bromo-N2,N2,N5,N5-tetrakis(2-methoxyethyl)pyrazine-2,5-dicarboxamide (26% yield) as a brown oil: LCMS (5-95% gradient acetonitrile in 0.1% TFA over 10 min), single peak retention time=3.85 min on 30 mm column, (M+H)+=608.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 111-95-5, its application will become more common.

Reference:
Patent; MediBeacon Inc.; Debreczeny, Martin P.; Rajagopalan, Raghavan; Dorshow, Richard B.; Neumann, William L.; Rogers, Thomas E.; (54 pag.)US2019/125901; (2019); A1;,
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Synthetic Route of 54314-84-0, A common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, molecular formula is C10H13BrO, 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.

Intermediate 104a: diethyl 2-(3-(benzyloxy)propyl)malonate To a suspension of sodium hydride (1.05 g, 26 mmol) in tetrahydrofuran (40 mL), was added diethyl malonate (7g, 44 mmol). Once evolution of gas had ceased, ((3- bromopropxy)methyl)benzene (5 g, 22 mmol) was added. The reaction mixture was heated in a 90 deg C bath for 6 h, then cooled to ambient temperature. The reaction was diluted with diethyl ether (100 mL) and washed with water (100 mL). The aqueous layer was separated and extracted with diethyl ether (2 x 100 mL). The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica-gel chromatography with ethyl acetate and heptanes as eluent to provide the desired compound. H NMR (400 MHz, CDCI3) delta 7.31-7.38 (m, 4H), 7.25-7.31 (m, 1 H), 4.50 (s, 2H), 4.10-4.27 (m, 7H), 3.50 (t, =6.3 Hz, 2H), 3.32-3.41 (m, 2H), 1.93-2.08 (m, 2H), 1.60 – 1.73 (m, 2H), 1.20- 1.38 (m, 10H) ppm.

The synthetic route of 54314-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BARYZA, Jeremy Lee; BECKWITH, Rohan Eric John; BOWMAN, Keith; BYERS, Crystal; FAZAL, Tanzina; GAMBER, Gabriel Grant; LEE, Cameron Chuck-Munn; TICHKULE, Ritesh Bhanudasji; VARGEESE, Chandra; WANG, Shuangxi; WEST, Laura; ZABAWA, Thomas; ZHAO, Junping; WO2014/136086; (2014); 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. 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,3-Dibromo-5-methoxybenzene

Tris [(DIBENZYLIDENEACETONE)] [DIPALLADIUM (0)] (6.53g, 7. [15MMOL)] was added in one portion to a stirred solution of the bromide of Preparation 1 (38. [0G,] [143MMOL),] 1,1′-bis (diphenylphosphino) ferrocene (9.3g, 16. [8MMOL)] and zinc cyanide (20. [OG,] [172MOL)] in N,N-dimethylformamide (300ml) at room temperature under nitrogen. The reaction was heated at [100°C] for 14 hours and cooled to room temperature. Water (1500ml) was added and the mixture was extracted with ethyl acetate (3x500ml). The combined organics were filtered and the filtrate was washed with water (500ml). dried over magnesium sulphate, filtered and concentrated under reduced pressure. The resulting solid was triturated with toluene [(1000ML)] to provide the title compound [(18. 0G)] as a tan solid. [1H-NMR (300MHZ, CDCI3)] : 8 = 3.83 (3H, s), 7.31 (2H, s), 7.48 (1 H, s).

According to the analysis of related databases, 74137-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.,; WO2004/29042; (2004); A1;,
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Reference of 52189-63-6,Some common heterocyclic compound, 52189-63-6, name is 1-Fluoro-3,5-dimethoxybenzene, molecular formula is C8H9FO2, 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.

[0321} Preparation of 5-fluorobenzene- 1 ,3-diol: To a solution of 1 -fluoro-3 ,5-dimethoxybenzene (2.0 g, 12.8 mmol) in dichloromethane (50 mL) cooled in a dry ice/acetone bath was added a solution of boron tribromide (2.8 mL, 29.0 mmol) in dichloromethane (50 mL) dropwise over half an hour. The reaction mixture was stirred over night during which reaction temperature raised to room temperature, and then cooled in a ice/water bath. 60 mL of methanol was added slowly.Organic solvents were evaporated under vaccum. The residue was extracted between ethyl acetate and aqueous sodium bicarbonate. The ethyl acetate phase was dried over sodium sulfate and evaporated to dryness. The crude product was purified by column chromatography with 0-40% ethyl acetate in hexanes to give desired product (1.6 g, 97% yield) LC-MS: 127 (M-H).

The synthetic route of 52189-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHROMOCELL CORPORATION; LUO, Robert, Zhiyong; CURRAN, Kevin, Joseph; HAYDEN, Stuart; YANG, Gengcheng; JIANG, Deshou; KRAL, Vincent; WO2014/153000; (2014); 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. 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, A new synthetic method of this compound is introduced below., SDS of cas: 1836-62-0

General procedure: Synthetic method: 1-alkyl-2-methyl-5-hydroxy-1H-indole-3-carboxylic acid 0.020 mol, O-methoxyphenoxyethylamine (12.16 g, 0.060 mol), N, N-dimethylformamide 10 mL and dichloromethane 100 mL were placed in a 250 mL eggplant flask, The HOBt (4.05 g, 0.030 mol), Triethylamine (6.07 g, 0.060 mol) EDCI (5.75 g, 0.030 mol) were added thereto, respectively, The reaction was stirred at room temperature for 16 h, The reaction solution was washed with a 2 mol / L aqueous hydrochloric acid solution and a saturated sodium bicarbonate solution, Add a large amount of water to stir the precipitated solid, Filter, Product crude ethanol recrystallization.

The synthetic route of 1836-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenyang Pharmaceutical University; Hu Chun; Zhang Lan; Ke Jia; Jin Zhe; Yao Dongming; Guo Wanxin; Liu Xiaoping; (35 pag.)CN106946761; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, 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 332-48-9, Computed Properties of C8H8BrFO

EXAMPLE 49 1-(2-(4-Fluorophenoxy)ethyl)-2-(hydroxymethyl)piperidine hydrobromide From 2-hydroxymethylpiperidine (500 mg, 4.34 mmol) and 2-(4-fluorophenoxy)ethyl bromide (999 mg, 4.56 mmol) there was obtained a colorless oil (970 mg, 88%): 1H NMR (CDCl3) d 1.60-2.11 (m, 6 H), 2.67-3.59 (m, 6 H), 3.80 (dd, J1=11 Hz, J2=3.9 Hz, 1 H), 4.15 (dd, J, =11 Hz, J2=3.9 Hz, 1 H) 4.37-4.42 (m, 2 H), 7.13-7.35 (m, 4 H). The hydrobromide was obtained as a colorless powder (1.08 g, 96%): mp 103.5-105.5 C.; Anal. Calcd for C14H21BrFNO2: C, 50.31; H, 6.33; N, 4.19. Found: C, 50.39; H, 6.15; N, 3.99.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2-Bromoethoxy)-4-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Warner-Lambert Co.; Cocensys, Inc.; US6218404; (2001); B1;,
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