Tag: M.W=100-200

Electric Literature of 28868-76-0,Some common heterocyclic compound, 28868-76-0, name is Dimethyl 2-chloromalonate, molecular formula is C5H7ClO4, 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.

c) 18.2 g of 2-chloro-5-methoxyphenol were dissolved in 150ml of dry methanol. 9.3 g of MeONa followed by 25 g of dimethyl chloromalonate were added. The reaction mixture was stirred at 50 C. for 2 hours. After distillation of the solvent the residue was partitioned between toluene and H2 O in a separating funnel and washed neutral. After crystallization in ethanol there was obtained dimethyl (2-chloro-5-methoxy)phenoxy-malonate, white crystals with m.p. 68-69 C.

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-chloromalonate, its application will become more common.

Reference:
Patent; Hoffmann-La Roche Inc.; US5541186; (1996); A;,
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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. 5121-34-6, name is Methyl 2-amino-3-methoxybenzoate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Step A:; To a solution of 2-amino-3-methoxybenzoate (1.62 g, 8.97 mmol) in DMF (15 mL) was added N-bromosuccinimide (1.76 g, 9.87 mmol). The resulting mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with ether and water. The aqueous layer was isolated and extracted with ether (2×100 mL). The combined organic layers were washed with water (2×100 mL), brine, dried over Na2SO4, filtered and concentrated to afford a brown solid. The crude material was purified by column chromatography (silica gel, 95:5 hexanes/ethyl acetate) to afford the desired product (2.08 g, 89%) as a light orange solid: 1H NMR (300 MHz, CDCl3) delta 7.60 (d, J=2.1 Hz, 1H), 6.90 (d, J=2.1 Hz, 1H), 6.03 (br s, 2H), 3.86 (s, 6H); MS (ESI+) m/z 259 (M+H).

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; AMR Technology, Inc.; US2006/183769; (2006); A1;,
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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 175867-59-1 as follows. Product Details of 175867-59-1

((R)-4-(5-(4-chlorophenyl)-1-ethyl-4-(3-(4-(4-(4-(4-(4-hydroxypiperidin-1-yl)-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonamido)phenyl)piperazin-1-yl)phenyl)-2-methyl-1H-pyrrole-3-carboxamido)cyclohexanecarboxylic acid (10) To a solution of BM-957 (100 mg, 0.09 mmol), EDCI (27 mg, 0.14 mmol) and HOBT (19 mg, 0.14 mmol) in DCM (2 mL) was added methyl 4-aminocyclohexanecarboxylate (44 mg, 0.28 mmol). The solution was stirred for 2 hours at room temperature until no BM-957 was observed by TLC. The reaction mixture was diluted with ethyl acetate (50 mL), washed with saturated NaHCO3 solution (50 mL), brine (50 mL) and dried over sodium sulfate. The solvent was removed in vacuo to give crude product which was used for next step without purification. The resulting residue was dissolved in H2O and MeOH (5 mL and 5 mL respectively) and followed by adding NaOH (76 mg, 1.9 mmol). The solution was stirred at room temperature for 20 h until no starting material was observed by TLC. The reaction mixture was concentrated in vacuo and the residue was purified by HPLC to give the pure product 10 (salt with TFA, 61 mg, yield 55% over two steps). The gradient ran from 60% of solvent A and 40% of solvent B to 20% of solvent A and 80% of solvent B in 40 min. MS (ESI): m/z 1191.17 (M+H)+.

According to the analysis of related databases, 175867-59-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; Wang, Shaomeng; Chen, Jianfang; McEachern, Donna; Bai, Longchuan; Liu, Liu; Sun, Duxin; Li, Xiaoqin; Aguilar, Angelo; US2014/199234; (2014); A1;,
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These common heterocyclic compound, 145576-28-9, name is Ethyl 4-methylenecyclohexanecarboxylate, 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. Application In Synthesis of Ethyl 4-methylenecyclohexanecarboxylate

Ethyl 4-methylidenecyclohexanecarboxylate (50 mg, 0.3 mmol) was stirred with 0.5M 9-borabicyclo[3.3.1]nonane in THF (0.89 mL), which was added slowly undernitrogen. The reaction mixture was stirred at room temperature overnight. The crude mixture was cooled to 0C and Intermediate 29 (203 mg, 0.51 mmol) in DMF (3 mL) was added, followed by bis[3 -(diphenylphosphanyl)cyclopenta-2,4-dien- 1 -yl] iron dichloropalladium dichloromethane complex (24 mg, 0.03 mmol) and 2M aqueous potassium carbonate solution (0.22 mL). The reaction mixture was stirred at room temperature overthe weekend, then heated at 60C for 1.5 h. Further bis[3-(diphenylphosphanyl)- cyclopenta-2,4-dien- 1 -yl]iron dichloropalladium dichloromethane complex (50 mg, 0.061 mmol) was added and the mixture was heated at 80C overnight under nitrogen. The reaction mixture was added to cold water and 0.5M aqueous NaOH solution (0.5 mL) was added. The mixture was extracted with DCM (100 mL), dried over sodium sulphate,filtered and concentrated under vacuum. The resulting brown oil was purified twice by FCC, eluting with 0-30% MeOH in DCM. The material was further purified by preparative HPLC (Method C), to afford the title compound (11.4 mg, 7%) as a brown oil. Method B HPLC-MS: MH+ m/z 535, RT 1.72 minutes.

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

Reference:
Patent; UCB PHARMA S.A.; BENTLEY, Jonathan Mark; BROOKINGS, Daniel Christopher; BROWN, Julien Alistair; CAIN, Thomas Paul; CHOVATIA, Praful Tulshi; FOLEY, Anne Marie; GALLIMORE, Ellen Olivia; GLEAVE, Laura Jane; HEIFETZ, Alexander; HORSLEY, Helen Tracey; HUTCHINGS, Martin Clive; JACKSON, Victoria Elizabeth; JOHNSON, James Andrew; JOHNSTONE, Craig; KROEPLIEN, Boris; LECOMTE, Fabien Claude; LEIGH, Deborah; LOWE, Martin Alexander; MADDEN, James; PORTER, John Robert; QUINCEY, Joanna Rachel; REED, Laura Claire; REUBERSON, James Thomas; RICHARDSON, Anthony John; RICHARDSON, Sarah Emily; SELBY, Matthew Duncan; SHAW, Michael Alan; ZHU, Zhaoning; WO2014/9295; (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. 13831-03-3, name is tert-Butyl propiolate, A new synthetic method of this compound is introduced below., Quality Control of tert-Butyl propiolate

General procedure: Into an oven-dried reaction flask under Ar gas protection was added oxabicyclic alkene (0.2 mmol), Au catalyst (0.001 mmol), methyl propiolate (0.4 mmol) and toluene (1.0 mL). The reaction mixture was stirred at room temperature normally overnight. After complete consumption of the starting materials, monitored by TLC, the solvent was removed under reduced pressure and the residue was purified by flash column chromatography.

The synthetic route of 13831-03-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sun, Yin-Wei; Xu, Qin; Shi, Min; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 1969 – 1976;,
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Electric Literature of 35179-98-7, The chemical industry reduces the impact on the environment during synthesis 35179-98-7, name is Chloromethyl ethyl carbonate, I believe this compound will play a more active role in future production and life.

Example 40: 4-((R)-3-(Bis-ethoxycarbonyloxymethoxy-phosphoryl)-2-{[4-((S)-3- methoxy-pyrrolidin-l-yl)-6-phenyl-pyridine-2-carbonyl]-amino}-propionyl)-piperazine- 1-carboxylic acid butyl ester:A solution of intermediate 22.2 (100 mg) in abs. DMPU (0.3 mL) and NEt3 (68 muL) was stirred for 10 min at RT. Then, chloromethyl ethyl carbonate (650 mg, prepared as described in WO2004092189) and NaI (29 mg) were added at RT, and the reaction mixture was stirred overnight at 500C. The reaction mixture was diluted with H2O and the aq. phase extracted with toluene. The combined organic layers were dried over Na2SC^ and concentrated to dryness. CC (EA) gave 19 mg of the desired product. LC-MS: tR = 0.97 min; [M+H]+: 822.32.

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, Chloromethyl ethyl carbonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/125366; (2009); A1;,
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Synthetic Route of 58656-98-7, A common heterocyclic compound, 58656-98-7, name is tert-Butyl 4-fluorobenzoate, molecular formula is C11H13FO2, 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.

816 g of the intermediate 2 was dissolved in 2500 g of o-dichlorobenzene, 900 g of aluminum trichloride was added, andthe o-dichlorobenzene solution of the intermediate 3 of the previous step was added dropwise to the reaction systemat 10-15 C. After the completion of the dropwise addition, thereaction was carried out at 10-15 C for about 3 hours.After the completion of the reaction, 2500 g of a 5.0% aqueous hydrochloric acid solution was added to the system, and the mixture was stirred for 10 minutes, allowed to stand for separation, and the organic phase was retained, and thesolvent was distilled off under reduced pressure at 100-120 C. O-dichlorobenzene was added to 2000 ethanol, heated to 75 C to dissolve, cooled to 0-5 C forcrystallization, and the filter cake was dried at 60 C to obtain 1248 g of intermediate 4.

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; Jiangsu Baozhongbaoda Pharmaceutical Co., Ltd.; Chen Rong; Zhao Haihua; Wang Lin; (8 pag.)CN109535081; (2019); A;,
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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. 4606-07-9, name is Ethyl cyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl cyclopropanecarboxylate

Example 2: Preparation of 2-bromo-1-cyclopropyl-2-(2-fluorophenyl) ethanone: Tetrahydrofuran (90 mL), magnesium turnings (4.4 g), and iodine are charged into a round bottom flask under nitrogen atmosphere at 28C. A solution of 2-bromopropane (22.07 g) in tetrahydrofuran (60 mL) is added to the reaction mass at 20C in 30 minutes and stirred at the same temperature for 1 hour. The solution of 2-(2-fluoro phenyl)acetic acid (11 g) [having less than 0.06% of 2-(3- fluorophenyl)acetic acid impurity] in tetrahydrofuran (20 mL) is added to the reaction mass at 20C in 30 minutes. The reaction mass is heated to 65C and stirred at the same temperature for 3 hours. The reaction mass is cooled to 5C. Ethyl cyciopropanecarboxylate (7.8 g) is added to the reaction mass in 10 minutes at 5C. The reaction mass is heated to 70C and stirred at the same temperature for 3 hours. The reaction mass is cooled to 20C. Water (10 mL) and 2N hydrochloric acid (90 mL) are added to the reaction mass at 20C and stirred for 20 minutes. The organic and aqueous layers are separated. The aqueous layer is extracted with dichloromethane twice (10 mL x 2). The combined organic layer is washed with saturated solution of sodium bicarbonate. The organic layer is dried over sodium sulfate. The solvent is evaporated under vacuum at 40C to get residue (6.8 g). Chloroform (130 ml) is added to the residue at 28C. N- bromo succinamide (7.8 g), azobisisobutyronitrile (0.39 g) and p-toluenesulfonic acid (0.19 g) are added to the reaction mass at 28 C. The reaction mass is heated to 65C and stirred at the same temperature for 4 hours. The reaction mass is cooled to 5C and stirred at the same temperature for 1 hour. The reaction mass is filtered at 5C to remove unwanted residue if any. The filtrate is washed with aqueous solution of sodium bisulfate (50 mL). The organic and aqueous layers are separated. The aqueous layer is extracted with chloroform (10 mL). The organic layers are combined and evaporated at 65C to get residue. Yield: 18.2 g; 2-bromo-1-cyclopropyl-2-(3-fluorophenyl)ethanone impurity. 0.051% by HPLC.

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 4606-07-9.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; ANUMULA, Raghupathi Reddy; GILLA, Goverdhan; AALLA, Sampath; METIL, Dattatray, Shamrao; KURELLA, Srinivas; CHARAGONDLA, Kavitha; WO2012/18791; (2012); A2;,
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These common heterocyclic compound, 35005-25-5, name is Isopropyl 3-aminobenzoate, 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. Formula: C10H13NO2

General procedure: To a suspension of carboxylic acid (100mg) and DMAP (6 eq) in DCM (0.2 M) under nitrogen at -15C was added T3P (3 eq)dropwise over a period of 20 min. The resulting mixture was stirred at -15Cuntil a solution was obtained (2h) and the aniline (3 eq) was added dropwise.The reaction mixture was stirred at -15 C for 1h, slowly warmed to roomtemperature and stirred overnight. Saturated aq. NaHCO3 was thenadded and the aqueous layer extracted with EtOAc. The organic phase was washedwith saturated aq. NH4Cl (x 2), NaHCO3 and brine, driedover Na2SO4, filtered and concentrated under vacuum. Theresidue was dissolved in DCM and purified by flash chromatography (DCM/MeOH97/3 to 92/8).

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

Reference:
Article; Boland, Sandro; Bourin, Arnaud; Alen, Jo; Geraets, Jacques; Schroeders, Pieter; Castermans, Karolien; Kindt, Nele; Boumans, Nicki; Panitti, Laura; Vanormelingen, Jessica; Fransen, Silke; Van De Velde, Sarah; Defert, Olivier; Bioorganic and Medicinal Chemistry Letters; vol. 25; 18; (2015); p. 4005 – 4010;,
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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. 5445-17-0, name is Methyl 2-bromopropanoate, A new synthetic method of this compound is introduced below., Computed Properties of C4H7BrO2

To a suspension of K2CO3 (3.6 g, 26.5 mmol) and tert- butyl piperazine-1-carboxylate (1.0 g, 5.3 mmol) in CH3CN (15 mL) was added methyl 2- bromopropanoate (2.2 g, 13.4 mmol). The reaction was stirred at 80 C for 10 hours. TLC showed that the reaction was complete. The reaction mixture was allowed to cool to room temperature, then the solid filtered off and solvent removed under vacuum. The residue was purified by silica gel column chromatography (CH2Cl2/MeOH = 50:1) to give tert-butyl 4-(1-methoxy-1-oxopropan-2-yl)piperazine-1- carboxylate (2-2) as a brown oil (1.4 g, yield: 99%).

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; KURA ONCOLOGY, INC.; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; WU, Tao; LI, Liansheng; WANG, Yi; REN, Pingda; GREMBECKA, Jolanta; CIERPICKI, Tomasz; KLOSSOWSKI, Szymon; POLLOCK, Jonathan; BORKIN, Dmitry; (198 pag.)WO2017/161028; (2017); A1;,
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