Month: November 2020

Adding a certain compound to certain chemical reactions, such as: 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, 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 653-92-9, 653-92-9

General procedure: A sealed tube of 25 mL equipped with a magnetic stir bar was charged with alkynes (0.20 mmol), 2-bromobenzoic esters (0.22 mmol), CuI (0.02 mmol, 10 mol%), NaOH (0.4 mmol, 2 equiv) and CH3CN (1.0 mL). The reaction mixture was stirred at 100 C for 24 h. The reaction was monitored by GC or GC-MS. After completion of the reaction, the reaction mixture was cooled to room temperature, then washed with saturated NH4Cl aqueous solution (5.0 mL), and extracted with CHCl3 (3 * 5.0 mL). The combined organic phases were dried over Na2SO4 (anhydrous), concentrated in vacuum. The crude product was purified by flash column chromatography (eluent: ethyl acetate/petroleum ether = 1/20-1/10) on silica gel to afford the desired product.

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

Reference:
Article; Sun, Mengli; Su, Lebin; Dong, Jianyu; Liu, Long; Zhou, Yongbo; Yin, Shuang-Feng; Tetrahedron Letters; vol. 58; 25; (2017); p. 2433 – 2437;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

61367-07-5, Name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, 61367-07-5, 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.

(1) To a solution of methyl trans-4-aminocyclohexanecarboxylate hydrochloride (1.0 g) obtained in Reference Example 2(1), triethylamine (1.1 ml), 30 % aqueous 3-hydroxypropionic acid solution (1.86 ml) in N,N-dimethylformamide (15 ml) are added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.19 g) and 1-hydroxybenzotriazole (837 mg) under ice-cooling. The mixture is then stirred at room temperature for 20 hours. The reaction solution is concentrated and saturated aqueous sodium hydrogen carbonate solution is poured to the residue, followed by extraction with chloroform. The organic layer is dried over sodium sulfate and evaporated to remove the solvent. The resulting residue is purified by silica gel column chromatography (eluent : ethyl acetate)to give methyl trans-4-[(3-hydroxypropanoyl)amino]cyclohexanecarboxylate (534 mg). APCI-MS M/Z : 230[M+H]+.

Statistics shows that Methyl trans-4-aminocyclohexanecarboxylate hydrochloride is playing an increasingly important role. we look forward to future research findings about 61367-07-5.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1582521; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 344-14-9, name is Dimethyl 2-fluoromalonate, This compound has unique chemical properties. The synthetic route is as follows., 344-14-9

General procedure: A test tube chargedwith MS 3A (40.0 mg, 200 mg/mmol) was flame-dried under reduced pressure using a heat gun. After cooling to room temperature, argon was re-filled, Schiff base 1 (11.1 mg, 0.02 mmol), THF (0.2 mL) andGd(OiPr)3 (0.2 M THF solution, 0.1 mL, 0.02 mmol) were added. The mixture was stirred at roomtemperature for 30 min to afford yellow suspension. THF was, then, removed under reduced pressure. Tothe test tube were added Y(OTf)3 (10.7 mg, 0.02 mmol) and THF (0.20 mL), and the mixture was stirred at room temperature for 30 min to afford the Gd(OiPr)3/Y(OTf)3/Schiff base = 1:1:1 catalyst in THF.Then, DMAP (2.4 mg, 0.02 mmol) was added, and THF was removed under reduced pressure. After drying the residue under reduced pressure for 1 h at room temperature, toluene (0.2 mL) and Et2O (0.4mL) were added. To the resulting red suspension were added 2-fluoromalonate 3 (0.35 mmol, 1.7 equiv)and meso-aziridine 2 (0.20 mmol, 1.0 equiv), and the mixture was stirred for 17-72 h at 40 C. After themixture was cooled to room temperature and diluted with AcOEt, saturated EDTA?2Na aq. was added.The organic layer was separated, and the aqueous layer was extracted with AcOEt and the organic layers were washed with brine. The organic layers were dried over Na2SO4. After filtration and evaporation, the obtained crude mixture was purified by silica gel column chromatography (AcOEt/hexane/CH2Cl2) togive a corresponding product.

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:
Article; Fukagawa, Seiya; Xu, Yingjie; Anada, Masahiro; Yoshino, Tatsuhiko; Matsunaga, Shigeki; Heterocycles; vol. 94; 7; (2017); p. 1337 – 1350;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 1190-39-2, name is malonic acid dibutyl ester, 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 1190-39-2. 1190-39-2

General procedure: PhIO (550 mg, 2.5 mmol), Et3N¡¤5HF (800 mg, 4 mmol), and DCE (1 mL)were placed in a Teflon test tube. After stirring at r.t. for 15 min, the appropriate malonic ester 1 (1 mmol) and DCE (1 mL) were added. The test tube was sealed with a septum rubber and heated at 70 C for 24 h with stirring. The reaction mixture was neutralized with aq NaHCO3 and the product was extracted with CH2Cl2 (3 ¡Á 10 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4), and concentrated under reduced pressure. The product was purified by column chromatography on silica gel with hexane-CH2Cl2 as eluent.

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 malonic acid dibutyl ester.

Reference:
Article; Kitamura, Tsugio; Muta, Kensuke; Oyamada, Juzo; Synthesis; vol. 47; 20; (2015); p. 3241 – 3245;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, 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. 609-12-1

Into a 100-mL round-bottom flask, was placed 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.9 g, 10.0 mmol, 1.00 equiv), N,N-dimethylformamide (30 mL), ethyl 2-bromo-3-methylbutanoate (2.1 g, 10.0 mmol, 1.0 equiv), and cesium carbonate (10.0 g, 30.7 mmol, 3.0 equiv). The resulting solution was stirred for 12 hours at 90 C. The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with ethyl acetate (20 mL*3), and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (1:6). This resulted in 3.3 g (93%) of ethyl 3-methyl-2-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butanoate as a white solid.

Statistics shows that 609-12-1 is playing an increasingly important role. we look forward to future research findings about Ethyl 2-bromo-3-methylbutanoate.

Reference:
Patent; Arvinas Operations, Inc.; Genentech, Inc.; Crew, Andrew P.; Wang, Jing; Berlin, Michael; Dragovich, Peter; Chen, Huifen; Staben, Leanna; US2019/300521; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common heterocyclic compound, 2318-25-4, name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, molecular formula is C7H14ClNO3, 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. 2318-25-4.

EXAMPLE 3F; Preparation of 5-ethoxythieno[3.2-b]pyridin-7-ol (3F3); Step A; To available thiophen-3-ylamine 3F1 (0.50 g, 5.04 mmol) was added imidate 3A2(1.08 g, 5.5 mmol) in ethanol (10 mL) under a N2 atmosphere. The mixture was stirred at RT. for 3 h at which point the reaction was concentrated. To the residue was added ether, and the suspension filtered and washed with ether to afford adduct 3F2(1.0g, 82percent). This material was sufficiently clean to be used in the subsequent step. MS: 242.1 (MH)+.

The synthetic route of Ethyl 3-ethoxy-3-iminopropionate hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2007/9227; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 344-14-9, name is Dimethyl 2-fluoromalonate, I believe this compound will play a more active role in future production and life. 344-14-9

Part B 2-(Difluoromethyl)-5-fluoro-6-hydroxy-4(1 H)-pyrimidinone Sodium metal (0.91 g, 40 mmol) was dissolved in MeOH (100 mL) to form sodium methoxide. 2,2-Difluoroethanimidamide HCI (1 .73 g, 13 mmol) was added followed by dimethyl fluoropropanedioate (2.0 g, 13 mmol). The resulting solution was stirred at 80 C for 3 hours, then cooled to room temperature. Aqueous HCI (6 mL, 6M, 36 mmol) was added and the resulting mixture was concentrated in vacuo. The remaining solid was washed with cold water and filtered yielding 2-(difluoromethyl)-5- fluoro-6-hydroxy-4(1 H)-pyrimidinone (1.43 g, 61 %)

The chemical industry reduces the impact on the environment during synthesis 344-14-9. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO. 2) LIMITED; AUBART, Kelly, Marshall; GILLIAN, Jason, Michael; QIN, Donghui; MCKEOWN, Robert, Rahn; WILLIAMS, Glenn, R.; WO2013/82388; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

816-27-3,Some common heterocyclic compound, 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, molecular formula is C6H11NO3, 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.

Step 1Ethyl F 1 ,2,4ltriazo loll ,5-alpyridine-2-carboxylate To solution of ethyl 2-ethoxy-2-iminoacete (1.91 g, 13.2 mmol) in ethanol (66.1 mL) was added1,2-diaminopyridinium iodide (2.35 g, 9.91 mmol) followed by potassium hydroxide (556 mg,9.91 mmol) and stirred at r.t. for 16 h. Water was then added, the mixture extracted with EtOAc, the organic layer was separated, and concentrated in vacuo. Purification by chromatography (silica, 60 100 % ethyl acetate in hexanes) gave ethyl [1,2,4]triazolo[1,5-a]pyridine-2- carboxylate (570 mg, 30 %). 1H NMR (400 MHz, CHLOROFORM-d) ppm 8.67 (dt, J=6.9, 1.2Hz, 1 H), 7.86 (dt,J=9.1, 1.2 Hz, 1 H), 7.62 (m, 1 H), 7.17 (td,J=7.0, 1.3 Hz, 1 H), 4.56 (q, J=7.2 Hz, 2 H), 1.48 (t, J=7.1 Hz, 3 H).

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BHAGIRATH, Niala; DOMINIQUE, Romyr; KENNEDY-SMITH, Joshua; LUCAS, Matthew C.; PADILLA, Fernando; WO2014/64134; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, 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. 61367-07-5

To a stirred solution of 6-((1,6-naphthyridin-2-yl)amino)-4-(cyclopropylamino)nicotinic acid (1.85 g, 5.76 mmol, Intermediate N) and methyl (1R,4R)-4-aminocyclohexane-1-carboxylate hydrochloride (1.34 g, 6.91 mmol) in DMF (10 mL) was added DIPEA (5 mL, 28.8 mmol) and PyBOP (4.5 g, 8.64 mmol) at rt. The resulting reaction mixture was stirred at rt for 16 h. The reaction mixture was then transferred into ice water and the resulting precipitate was filtered off, and dried reduced pressure. The crude product was purified using silica gel column chromatography (7% MeOH-DCM) to give methyl (1r,4r)-4-(6-((1,6-naphthyridin-2-yl)amino)-4-(cyclopropylamino)nicotinamido)cyclohexane-1-carboxylate as light a green solid (1.3 g, 49%). LC-MS (ESI+) m/z 460.54 (M+H)+

Statistics shows that 61367-07-5 is playing an increasingly important role. we look forward to future research findings about Methyl trans-4-aminocyclohexanecarboxylate hydrochloride.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

59247-47-1, Adding some certain compound to certain chemical reactions, such as: 59247-47-1, name is tert-Butyl 4-bromobenzoate, 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 59247-47-1.

To a mixture of tert-butyl 4-bromobenzoate (10.07 g, 39.2 mmol), K3PO4 (20.19 g, 95 mmol), and dimethyl malonate (4.50 mL, 39.2 mmol) was added toluene (69 mL), Pd2(dba)3 (975 mg, 1.08 mmol), and .yen.(tert-Bu)3 (12.8 mL, 10percent wt. in hexanes, 4.3 mmol). The reaction mixture was degassed and heated to 85¡ãC. After 2 d, the reaction mixture was diluted with ethyl acetate, washed with water (1 x), brine (1 x), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (5percent to 20percent ethyl acetate in hexanes) gave dimethyl [4-(fe/t-butoxycarbonyl)phenyl]malonate as a low melting white solid: 1HNMR (600 MHz, CDCl3) delta 7.98 (d, J = 8.5 Hz, 2H), 7.45 (d, J = 8.2 Hz, 2H), 4.70 (s, IH), 3.76 (s, 6H), 1.58 (s, 9H); ESIMS calcd 331.1 (Mi + Na), found 331.1 (Mi + Na).

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 59247-47-1.

Reference:
Patent; MERCK & CO., INC.; WO2007/55941; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics