Tag: M.W=200-300

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. 179022-43-6, name is Methyl 8-azabicyclo[3.2.1]octane-3-carboxylate hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 8-azabicyclo[3.2.1]octane-3-carboxylate hydrochloride

A mixture of (3-bromo-lH-pyrazolo[4,3-b]pyridin-l-yl)(2-chloro-6-(trifluoromethyl) phenyl)methanone (B-1) (200mg, 0.50mmol), 3-(methoxycarbonyl)-8-azonia- bicyclo[3.2.1]octane chloride 2 (0.15 g, 0.75 mmol) and Cs2C03 (0.65g, 2.0mmol) were suspended in DMF (5mL). The reaction mixture was heated at 150C in a microwave reactor for 5h. The result mixture was diluted with H20 (50mL). 2M HCl solution was added to adjust the pH~3 and the aqueous layer was extracted with ethyl acetate (3x20mL). The combined organic layers were washed with brine (20mL), dried over anhydrous Na2S04 and concentrated to get the crude product B-2 as yellow oil. LCMS (ESI) calc’d for C23H20ClF3N4O3 [M+H]+: 493, found: 493

According to the analysis of related databases, 179022-43-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; WO2014/26330; (2014); A1;,
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773873-95-3, name is Methyl 2,2-difluorobenzo[d][1,3]dioxole-5-carboxylate, belongs to esters-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. Product Details of 773873-95-3

Crude 2,2-difluoro-benzo[1,3]dioxole-5-carboxylic acid methyl ester (11.5 g) dissolved in 20 mL of anhydrous tetrahydrofuran (THF) was slowly added to a suspension of lithium aluminum hydride (4.10 g, 106 mmol) in anhydrous THF (100 mL) at 0 C. The mixture was then warmed to room temperature. After being stirred at room temperature for 1 hour, the reaction mixture was cooled to 0 C. and treated with water (4.1 g), followed by sodium hydroxide (10% aqueous solution, 4.1 mL). The resulting slurry was filtered and washed with THF. The combined filtrate was evaporated to dryness and the residue was purified by silica gel column chromatography to give (2,2-difluoro-benzo[1,3]dioxol-5-yl)-methanol (7.2 g, 38 mmol, 76% over two steps) as a colorless oil.

The synthetic route of 773873-95-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hadida Ruah, Sara S.; Grootenhuis, Peter D.J.; Van Goor, Frederick; Zhou, Jinglan; Bear, Brian; Miller, Mark T.; McCartney, Jason; Numa, Mehdi Michel Jamel; US2007/244159; (2007); 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. 29823-21-0, name is Ethyl 8-Bromooctanoate, A new synthetic method of this compound is introduced below., Recommanded Product: 29823-21-0

Example 15Synthesis of Ethyl 8-nitrooxy-octanoate; 20.0 mmol Ethyl 8-bromooctanoate dissolved in 80 ml acetonitrile and 50.0 mmol silver nitrite were added into a flask protected from light. This suspension was stirred for 18 hours at 70 C. After cooling to room temperature the suspension was filtrated over silica gel, washed with Ethylacetate and concentrated in vacuo.The crude product was purified by flash chromatography on silica gel using heptane/ethyl acetate 4:1; Yield: 4.35 g (18.6 mmol, 93.2%).

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; Duval, Stephane; Kindermann, Maik; US2012/315339; (2012); A1;,
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Synthetic Route of 139102-34-4, 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 139102-34-4 as follows.

Example 25A methyl 4-(4-((4′-chlorobiphenyl-2-yl)methyl)piperazin-1-yl)-2-methoxybenzoate Methyl 4-bromo-2-methoxybenzoate (700 mg), EXAMPLE 7B (983 mg), K3PO4 (909 mg), tris(dibenzylideneacetone)dipalladium(0) (78 mg), and 2-(di-t-butylphosphino)biphenyl (102 mg) were stirred in 1,2-dimethoxyethane (10 mL) at 80 C. for 24 hours. The reaction mixture was chromatographed on silica gel with 20-50% ethyl acetate/hexanes.

According to the analysis of related databases, 139102-34-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; US2010/184750; (2010); 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. 1139-13-5, name is Diethyl cyclohexane-1,1-dicarboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C12H20O4

Example 9 Preparation of 1-fluoromethylcvclohexylalanine P2 building block Cyclohexane-1,1-dicarboxylic acid diethyl ester,1 , was prepared in accordance with JACS 43, 1921, 1368 from diethyl malonate and 1 ,5-dibromopentane.Cyclohexane-1,1-dicarboxylic acid diethyl ester, 1 , was taken up in anhydrous THF under nitrogen at room temperature. This was treated with LiAI(O1Bu)3H (2.5eq) portionwise before refluxing overnight. The reaction mixture was cooled in an ice-bath and treated carefully with 10% KHSO4(aq) and allowed to stir for 10 minutes. The resulting precipitate was removed by vacuum filtration and the mother liquors were partitioned between EtOAc and brine. The organic phases were combined, dried over MgS04, filtered and concentrated in vacuo to give a mobile oil. This was purified by flash column chromatography to give 1-hydroxymethyl- cyclohexanecarboxylic acid ethyl ester, 2 as a colourless oil (51%). EPO 1-Hydroxymethyl-cyclohexanecarboxylic acid ethyl ester, 2 was taken up in [bis (2- methoxyethyl) amino] sulphur trifluoride and heated overnight at 7O0C. The reaction was then allowed to cool to O0C and carefully treated with saturated NaHCO3 (aq) dropwise. This was stirred at room temperature for 30 minutes. The mixture was washed twice with DCM and the combined organics were washed with saturated NaHCO3 (aq) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography to give 1 -fluoromethyl-cyclohexane carboxylic acid ethyl ester, 3, as a colourless oil (34%)1-Fluoromethyl-cyclohexane carboxylic acid ethyl ester, 3, was dissolved in anhydrous THF and cooled under a nitrogen atmosphere to O0C. This was treated portionwise with LiAIH4 (2eq) and warmed to room temperature for 4 hours. After this time the reaction was cooled to O0C and carefully treated with 2M HCI(aq) and stirred for 20 minutes. The reaction was filtered through a pad of celite and the pad was washed with diethyl ether. The collected solution was partitioned between brine and diethyl ether. The combined organic phases were dried over MgSO4, filtered and concentrated in vacuo to give an oil. This was purified by flash chromatography to give (1- fluoromethyl-cyclohexyl) methanol, 4, as a colourless oil (67%).(1 -Fluoromethyl-cyclohexyl) methanol, 4, was dissolved in anhydrous DCM under N2 and cooled to -2O0C. NEt3 (1.1eq) was added and the reaction was stirred for 5 minutes. This was then treated dropwise with triflic anhydride (1 1eq) and the solution was stirred at O0C for 1hour. The reaction mixture was poured onto ice and the organics were washed with 1M HCI (aq), saturated NaHCO3 (aq) and brine, then dried over MgSO4, filtered and concentrated in vacuo, to give trifluoro-methanesulfonic acid-1-fluoromethyl-cyclohexylmethyl ester, 5, as an amber oil which was used immediately without further purification in the next step.N-(Diphenylmethylene)glycine ethyl ester was dissolved in DMF and under a nitrogen atmosphere was cooled to O0C. This was treated with KO’Bu (1.1eq) and stirred for 20 minutes. To this solution was added trifluoro-methanesulfonic acid-1-fluoromethyl-cyclohexylmethyl ester, 5 dropwise. The reaction mixture was stirred at room temperature under nitrogen overnight then poured into a 1 :1 mixture of diethyl ether : NH4CI (aq). The phases were separated and the aqueous phase was washed twice with diethyl ether. The organic phases were combined and washed several times with brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was purified by flash column chromatography to give 2-(benzhydrylidene- amino)-3-(1 fluoromethyl-cyclohexyl) propionic acid ethyl ester, 6 (28%).2- (Benzhydrylidene-amino)-3-(1-fluoromethyl-cyclohexyl)propionic acid ethyl ester, 6, was taken up in 1,4-dioxan and treated with 2 M NaOH (aq) (2eq) with stirring. After the starting EPO material had been consumed (tic), the reaction mixture was acidified by addition of 2M HCI (aq) and stirred overnight at room temperature. The solution was concentrated in vacuo and the residue was partitioned between TBME and water. The pH of the aqueous phase was adjusted to p H 7 by careful addition of 2M NaOH (aq) prior to lyophilisation. The resulting residue was then suspended in 10% Na2CO3 (aq) and dioxan until a homogeneous solution was obtained. Fmoc chloride was added portion wise to the ice-cooled solution over 12 hrs and this was allowed to stir at room temperature overnight. The reaction mixture was washed with TBME and the resulting aqueous was acidified with 2M HCI (aq) and allowed to freeze dry. The resulting solid was triturated with methanol and the mother liquors were collected by filtration and concentrated in vacuo. To remove last traces of salts the resulting solids were partitioned between water and ethyl acetate. The organics were dried over MgSO4, filtered and concentrated in vacuo to give 2-(9H-fluoren-9-ylmethoxycarbonylamino)-…

The synthetic route of 1139-13-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVIR UK Ltd; PEPTIMMUNE, Inc; WO2006/64286; (2006); 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. 19063-56-0, name is 7-Bromo-2H-chromen-2-one, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H5BrO2

N-butyl-1,8-naphthalimide borate 11 (0.2 g, 0.53 mmol), 7-bromocoumarin(0.12 g, 0.53 mmol), Pd(PPh3)4 (0.024 g, 4 mol%) and 2Msodium carbonate solution (4 mL) were dissolved in THF (20 mL). Thereaction mixture was left for 8 h under nitrogen atmosphere at 70 C.After completion of the reaction, the reaction mixture was cooled toroom temperature and poured into water (50 mL), then extracted withdichloromethane (50 mLx 2). The organic layer was separated, washedwith saturated brine solution, dried over Na2SO4 and concentrated invacuum. The resulting residue was purified by column chromatographyon silica gel with hexane: ethyl acetate (8:2, v/v) as eluant. NC 4 wasobtained in 52.5% yield (0.11 g), m. p. 222 C. IR (KBr): numax/cm-11729 (nuCO), 1691 (nuCO). 1H NMR (400 MHz, CDCl3) delta 8.687-8.658 (m,2H, aromatic), 8.218 (d, 1H, J=8.8 Hz, aromatic), 7.836 (d, 1H,J=9.6 Hz, aromatic), 7.766-7.672 (m, 3H, aromatic), 7.503 (s, 1H,aromatic), 7.447 (d, J=8 Hz, 1H, aromatic), 6.546 (d, 1H, J=9.6 Hz),4.224 (t, 2H, J=7.6 Hz, CH2), 1.788-1.712 (m, 2H, CH2), 1.521-1.446(m, 2H, CH2), 0.996 (t, 3H, J=7.6 Hz, CH3)·13C (150 MHz, CDCl3) delta164.11, 163.88, 160.36, 154.01, 144.40, 142.87, 142.59, 131.77,131.41, 130.64, 129.63, 128.64, 128.10, 127.92, 127.35, 126.08,123.10, 122.66, 118.73, 118.20, 117.45, 40.34, 30.17, 20.37, 13.84.HRMS (m/z): [M+H] calculated for C25H20NO4: 398.1392; Found:398.1384

The synthetic route of 19063-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reddy, T. Sheshashena; Hwang, Jiyoung; Choi, Myung?Seok; Dyes and Pigments; vol. 158; (2018); p. 412 – 419;,
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Electric Literature of 21905-56-6, 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. 21905-56-6, name is Methyl 2-phenoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2 2-Phenoxybenzylalcohol A 1.0 M solution of lithium aluminum hydride in THF (25 ml, 25 mmol) was added to a solution of crude 2-phenoxybenzoic acid methyl ester (5.23 g, 22.9 mmol) in THF. The reaction mixture was stirred for 2.5 hours at room temperature. Methanol (10 ml) was added carefully. THF (50 ml) was added. Magnesium sulphate was added. The solids were filtered off. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (90 g), using ethyl acetate/heptane (1:1) as eluent, to give 4.08 g of 2-phenoxybenzylalcohol. 1H NMR (CDCl3) delta 4.70 (m, 2 H); 6.85 (d, 1 H); 6.97 (d, 2 H); 7.10 (m, 2 H); 7.25 (t, 1 H); 7.35 (t, 2 H); 7.45 (d, 1 H).

The synthetic route of Methyl 2-phenoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Andersen, Knud Erik; Dorwald, Florencio Zaragoza; Peschke, Bernd; US2001/49385; (2001); A1;,
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Adding a certain compound to certain chemical reactions, such as: 46064-79-3, name is Methyl 3-amino-4-bromobenzoate, belongs to esters-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 46064-79-3, Safety of Methyl 3-amino-4-bromobenzoate

Methyl 3-amino-4-bromobenzoate (4 g, 17.39 mmol), (3-fluoropyridin-4- yl)boronic acid (5.5 g, 39.0 mmol), dioxane (10 mL), water (2 mL) and potassium carbonate (8.41 g, 60.9 mmol) were taken in a dried two neck RB (25mL) and purged with nitrogen for 10 minutes. To this mixture was added PdCi2(dppf) (1.27 g, 1.74 mmol) at 50 C. The mixture was flushed with nitrogen and heated at 80 C for 8 h. The reaction mixture was cooled to room temperature, then was diluted with the DCM. The organic phase was washed with the water, dried over sodium sulphate. The crude compound was purified by silica gel chromatography (ethyl acetate/petroleum ether, (30-65%) to afford 2.9 g (68%) of the title compound. LC-MS (ESI) m/z: 241.0 [M+H]+; XH NMR (400 MHz, chloroform-d) delta ppm 8.60 (d, J=1.57 Hz, 1 H) 8.52 (dd, J=4.86, 1.10 Hz, 1H) 7.48 – 7.52 (m, 2 H) 7.35 – 7.39 (m, 1H) 7.19 (d, J=7.78 Hz, 1H) 3.93 (s, 3 H) 3.79 – 3.84 (m, 2 H).

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; BRISTOL-MYERS SQUIBB COMPANY; QUAN, Mimi L.; HU, Zilun; WANG, Cailan; WO2015/2926; (2015); A1;,
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Synthetic Route of 6942-37-6,Some common heterocyclic compound, 6942-37-6, name is Methyl 5-amino-2-bromobenzoate, molecular formula is C8H8BrNO2, 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 solution of the aniline compound (1O g = 43.48 mmol) and triethylamine (TEA. 11.53 ml. = 86.96 mmol) in 100 ml. of toluene, 1 ,4-dibromobutane (10.39 ml. = 86.96 mmol) was added. The reaction mixture was heated to 100 0C for 5 h. The resulting reaction mixture was concentrated, re-diluted with ethyl acetate, washed with saturated NaHCOs aqueous solution and NaCI aqueous solution, dried over MgSO4, then filtered and concentrated. The residue was chromatographed over a 120 g silica column, eluting with 20 % ethyl acetate in hexane to provide 7.1 g of the product 2-(4-pyrrolidin-1-yl-2-methylhydroxy- phenyl)-4,5,6-tetrahydro-thiazolo[4,5-c]pyridin-7-ol as a light yellow solid, MS: m/z 284.1 , 286.1 (M+H).

The synthetic route of 6942-37-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; WO2009/120849; (2009); A1;,
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Application of 139102-34-4, 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. 139102-34-4, name is Methyl 4-bromo-2-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under the protection of nitrogen,Compound 49E (150 mg, 0.66 mmol),Methyl 4-bromo-2-methoxybenzoate (168 mg, 0.69 mmol),Palladium acetate (15 mg, 0.066 mmol), BINAP (42 mg, 0.066 mmol),Barium carbonate (324mg, 0.99mmol)The 1,4-dioxane solution was heated to 110 C for 4 hours and then lowered to room temperature.The reaction was quenched with EtOAc (EtOAc)EtOAc.The compound was quenched under reduced pressure to give compound 49F (90 mg, 35% yield)

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, Methyl 4-bromo-2-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jiangsu Xiansheng Pharmaceutical Co., Ltd.; Chen Huanming; Liang Bo; Cao Wenjie; Zhang Guiping; Zhao Zhongqiang; Jiang Zhaojian; Zuo Gaolei; Xu Wanmei; Gong Hongju; Zhang Peng; Wang Jianghuai; Li Qingsong; Gao Chunhua; (79 pag.)CN104045552; (2019); B;,
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