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. 369-25-5, name is Methyl 3,4-difluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H6F2O2

a) 3-Fluoro-4-dimethylamino-benzoic acid methyl ester (3a) To a stirred solution of 38,7g (225 mmol) 3.4-difluoro-benzoic acid methyl ester (Apollo) and 600 ml dimethylsulphoxid are added 22.3 g (270 mmol) dimethylamine hydrochloride and 65.4 g (473 mmol) potassium carbonate. The reaction mixture is stirred for 5h at 55C in an autoclave and is reduced with high vacuum rotation evaporator at 65C. The residue is diluted with dichloromethane, washed twice with water. The combined water phases are extracted with dichloromethane. The combined dichloromethane phases are washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude product 3a is obtained in 71% yield (31.5 g, 160.0 mmol) and is used for the next step without purification. MS-ESI: 198 (M+ +1, 72).

The synthetic route of 369-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; EP1897885; (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. 22223-49-0, name is Methyl 2-amino-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H11NO2

To a solution of methyl 2-amino-3-methylbenzoate (4) (1.00 g, 6.10 mmol) in DMF (10 ml) was added NBS (1.10 g, 6.10 mmol), and the reaction mixture was stirred at rt for 6 h. The reaction mixture was diluted with EtOAc (10 ml) and washed with saturated aqueous Na2CO3 solution (10 ml * 3). The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexanes/EtOAc = 100:1) to give compound 5 as pale gray solid (0.93 g, 62% yield): 1H NMR (400 MHz, CDCl3) delta (ppm) 7.88 (d, J = 2.3 Hz, 1H), 7.28 (d, J = 2.3 Hz, 1H), 5.82 (s, 2H), 3.86 (s, 3H), 2.15 (s, 3H).

According to the analysis of related databases, 22223-49-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kim, Mi Kyoung; Shin, Heerim; Cho, Seo Young; Chong, Youhoon; Bioorganic and Medicinal Chemistry; vol. 22; 3; (2014); p. 1156 – 1162;,
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Synthetic Route of 33689-29-1, 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 33689-29-1 as follows.

Example B6 A 0 C. solution of methyl 1-hydroxycyclopropane-1-carboxylate (1 g, 8.61 mmol) in DMF (10 mL) was treated with NaH (60% in mineral oil, 0.689 g, 17.22 mmol), stirred at 0 C. for 0.5 h, treated with iodomethane (0.646 mL, 10.33 mmol), allowed to slowly warm to RT and stirred for 2 h. The mixture was quenched with satd. NH4Cl, diluted with water and extracted with Et2O (3*). The combined organics were washed with water, then brine, dried and concentrated to afford methyl 1-methoxycyclopropane-1-carboxylate (1.10 g, 98%). 1H NMR (400 MHz, DMSO-d6): delta 3.62 (s, 3H), 3.27 (s, 3H), 1.12-1.11 (m, 4H).

According to the analysis of related databases, 33689-29-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Kaufman, Michael D.; Patt, William C.; Ahn, YuMi; US2014/275016; (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. 10601-80-6, name is Ethyl 3,3-diethoxypropionate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Ethyl 3,3-diethoxypropionate

General procedure: A mixture of montmorillonite K-10 (75 mg), an appropriate aniline 1 (150 mg, 1.2 mmol), ethyl-3,3-diethoxypropionate (3) (579 mg, 3 mmol) and an aldehyde (166 mg, 1.34 mmol) in pure water (7.5 mL) was stirred at 90 C for the time mentioned in Table 2. After completion of the reaction (indicated by TLC), the mixture was cooled to room temperature and filtered. The filtrate was extracted with EtOAc (3 ¡Á 5 mL). The organic layers were collected, combined, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate-hexane to give the desired product.

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 10601-80-6.

Reference:
Article; Reddy, T. Ram; Reddy, G. Rajeshwar; Reddy, L. Srinivasula; Meda, Chandana Lakshmi T.; Parsa, Kishore V.L.; Kumar, K. Shiva; Lingappa; Pal, Manojit; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 395 – 404;,
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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. 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H8ClNO2

To an ice-cold aqueous solution of concentrated hydrochloric acid (30 mL) was added compound 2 (7.4 g, 40 mmol), followed by the dropwise addition of sodium nitrite (3.036 g, 44.0 mmol) in distilled water (5 mL). After 0.5 h of stirring at 0 C, tin(II) chloride (18.05 g, 80 mmol) in concentrated hydrochloric acid (30 mL) was added dropwise to the above solution. The reaction was stirred for 4 h at 0 C and filtered and successively washed with concentrated hydrochloric acid (15 mL). The precipitate was dissolved in distilled water and filtered. When the filtrate was adjusted to pH 13 by adding 4 mol/L sodium hydroxide under stirring, a large amount of solid formed and was filtered and dried to obtain compound 3. White solid, yield: 63.9%, m.p.132-133 C. 1H NMR (400 MHz, CDCl3) delta 7.76 (s, 1H, Ph-H), 7.40 (d, J = 8.2 Hz, 1H, Ph-H), 7.35 – 7.23 (m, 1H, Ph-H), 5.81 (s, 1H, NH), 3.91 (s, 3H, OCH3), 3.67 (s, 2H, NH2).

The synthetic route of 40872-87-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Feng-Yun; Wang, Yuan-Hong; Liu, Jing-Bo; Li, Yu-Xin; Li, Zheng-Ming; Bioorganic and Medicinal Chemistry; vol. 27; 5; (2019); p. 769 – 776;,
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Synthetic Route of 35613-44-6, 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. 35613-44-6, name is Methyl 2-(2-aminophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 7.2 g of 4-chloro-7-trifluoromethylquinoline, 5.4 g of methyl 2- aminophenylacetate and 250 mL of acetonitrile is heated under reflux for 18 hours. The solvent is evaporated under reduced pressure and the residue extracted 3 times with 200 mL portions of hot water. The aqueous extract is rendered basic with 10% ammonium hydroxide whereupon the desired compound precipitated; it was recrystallized from aqueous ethanol yielding colorless needles with a melting point of 140-1410C.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-(2-aminophenyl)acetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MILESTONE PHARMACEUTICALS INC.; WO2008/48577; (2008); A1;,
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Electric Literature of 344-14-9,Some common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, molecular formula is C5H7FO4, 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 224 Synthesis of dimethyl 2-((2-((4-(tert-butoxycarbonyl)-1H-1,2,3-triazol-1-yl)methyl)-6-cyclopropylimidazo[1,2-a]pyridin-8-yl)methyl)-2-fluoromalonate. To a solution of compound dimethyl 2-fluoromalonate (0.54 g, 3.6 mmol) in anhydrous DMF (10 mL) was added NaH (140 mg, 3.6 mmol, 60% in mineral oil) and the reaction was stirred at 0 C. for 0.5 h under N2 atmosphere. Then the solution of tert-butyl 1-((8-(chloromethyl)-6-cyclopropylimidazo[1,2-a]pyridin-2-yl)methyl)-1H-1,2,3-triazole-4-carboxylate (1 g, 2.5 mmol) in DMF (2 mL) was added, The resulting mixture was stirred at 80 C. for 16 h. The reaction was quenched with saturated aqueous NH4Cl solution (20 mL), and extracted with ethyl acetate (100 mL*2). The combined organic phases were dried over Na2SO4, evaporated to give the crude, which was purified with silica gel chromatography (DCM/MeOH=100/1) to give the dimethyl 2-((2-((4-(tert-butoxycarbonyl)-1H-1,2,3-triazol-1-yl)methyl)-6-cyclopropylimidazo[1,2-a]pyridin-8-yl)methyl)-2-fluoromalonate (1.1 g, 85%) as a yellow solids. ESI-MS [M+H]+: 502.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl 2-fluoromalonate, its application will become more common.

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
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Electric Literature of 33842-16-9, The chemical industry reduces the impact on the environment during synthesis 33842-16-9, name is Methyl benzo[d][1,3]dioxole-4-carboxylate, I believe this compound will play a more active role in future production and life.

A solution of methyl benzo[ ][1 ,3]dioxole-4-carboxylate (0.4 g, 2.22 mmol) in methanol (8.0 mL) was treated with 2.0 M aqueous KOH (2.2 mL) and the solution stirred at rt for 3 hours. The mixture was concentrated to ~3 mL volume, diluted with water (5 mL) and acidified to pH ~3 using 2.0 M HCI. The resulting precipitate was removed by filtration, washed with water then diethyl ether and dried in vacuo to give benzo[ ][1 ,3]dioxole-4-carboxylic acid as a beige solid (0.38 g, 97%).1H NMR (400 MHz, DMSO-d6): delta = 7.28 (dd, J= 8.0, 1.2 Hz, 1H),6.97 (dd, J=8.0, 1.2 Hz, 1H),6.89 (t, J=8.0Hz, 1 H), 6.12 (s, 2H);13C NMR(100 Hz, DMSO-de) 165.5, 148.9, 148.5, 122.9, 121.6, 113.8, 112.5, 102.1.

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 benzo[d][1,3]dioxole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNIVERSITY OF QUEENSLAND; THE PROVOST, FELLOWS, FOUNDATION SCHOLARS, AND THE OTHER MEMBERS OF BOARD, OF THE COLLEGE OF THE HOLY AND UNDIVIDED TRINITY OF QUEEN ELIZABETH NEAR DUBLIN; O’NEILL, Luke; COLL, Rebecca; COOPER, Matt; ROBERTSON, Avril; SCHRODER, Kate; (379 pag.)WO2016/131098; (2016); A1;,
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Synthetic Route of 36692-49-6, 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. 36692-49-6, name is Methyl 3,4-diaminobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In 25 ml round-bottomed flask, a mixture of 1,2-phenylendiamine (1 mmol), a-bromoacetophenone(1 mmol) and BAILnano-SiO2 catalyst (35 mol%) was preparedand the reaction mixture was stirred at room temperature for the time shown inTable 2. The progress of the reaction was monitored by TLC. After completion of the reaction, ethyl acetate (5 mL) was added and the catalyst was separated by simplefiltration. The residue was dried over anhydrous Na2SO4 and after evaporation ofsolvent the pure product was obtained by recrystallization from ethanol.

The chemical industry reduces the impact on the environment during synthesis Methyl 3,4-diaminobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Daragahi, Seyed Arash Hosseini; Mohebat, Razieh; Mosslemin, Mohammad Hossein; Organic Preparations and Procedures International; vol. 50; 3; (2018); p. 301 – 313;,
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1117-71-1, name is Methyl 4-bromobut-2-enoate, 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. Quality Control of Methyl 4-bromobut-2-enoate

To the suspension of potassium phthalimide (4.5 mmol) in dry DMF (4 mL) was added a solution of (E)-alkyl -bromobut-2-enoate in dry DMF (3 mL). The reaction was run at room temperature overnight. After the reaction was omplete, the reaction mixture was poured into water and extracted with ether and concentrated in vacuum to leave a hite solid. The residue can be easily purified by flash chromatography (petroleum/ethyl acetate, 4:1), to give the desired compounds 1.

The synthetic route of 1117-71-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Fuzhong; Chen, Jun; Zhang, Xiangyang; Liu, Jibing; Cun, Linfeng; Zhu, Jin; Deng, Jingen; Liao, Jian; Tetrahedron Letters; vol. 52; 7; (2011); p. 830 – 833;,
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