Author: Jessica.F

Related Products of 756525-95-8,Some common heterocyclic compound, 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, molecular formula is C11H23NO4, 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.

To a stirred solution of 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido- )phenoxy)picolinic acid (08) (200 mg, 0.44 mmol, 1.0 equiv) in DMF (5.0 mL, 25.0 vol. equiv.) were added tert-butyl 3-(2-(2-aminoethoxy)ethoxy)propanoate (10) (124 mg, 0.53 mmol, 1.2 equiv), HATU (505 mg, 1.33 mmol, 3.0 equiv) and DIPEA (68.5 mg, 0.53 mmol, 1.20 equiv). The reaction mixture was stirred for 12h at RT. Completion of reaction was monitored by TLC. The Reaction mixture was quenched with DMW (100 mL) and extracted with EtOAc (100 mL x 3). The combined organic extract was washed with brine (100 mL), dried over Na2S04 and concentrated under vacuum to afford the desired compound (11) (290 mg, 98.20%) as a brown gum. MR (300 MHz, OMSO-d6) delta 9.22 (s, 1H), 9.00 (s, 1H), 8.69 (s, 1H), 8.52-8.51 (d, 1H), 8.13-8.12 (d, 1H), 7.65-7.64 (d, 2H), 7.63 (s, 1H), 7.61-7.60 (d, 1H), 7.58 (s, 1H), 7.39-7.38 (d, 1H), 7.19-7.16 (m, 3H), 3.59-3.41 (m, 16H), 2.89 (s, 2H), 2.41-2.39 (d, 2H) 1.40-1.37 (t, 9H). MS (ES+): 755.0 (M+l); MS (ES-): 753.2 (M-l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 9-Amino-4,7-dioxanonanoate, its application will become more common.

Reference:
Patent; QUARTZ THERAPEUTICS, INC.; ZAMBONI, Robert; HENNING, Ryan; JI, Alan; SMITH, Tyler; HELLER, Bradley; REDDY, Thumkunta Jagadeeswar; ROCHELEAU, Sylvain; BEAULIEU, Marc Andre; (266 pag.)WO2018/200981; (2018); 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. 5164-76-1, name is Dimethyl pent-2-enedioate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 5164-76-1

General procedure: The crude aryl diazonium tosylate 9 thus obtained was dissolved or suspended in MeOH (30 mL). Dimethyl glutaconate (1.45 mL, 10.0 mmol) and Pd(OAc)2 (112 mg, 0.5 mmol) were successively added while stirring. After stirring at r.t. for 15 h, the mixture was concentrated under reduced pressure and partitioned between CH2Cl2 (40 mL) and H2O (25 mL). The organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was briefly fractionated on SiO2 using CH2Cl2 or CH2Cl2- acetone (5:1) as eluent. Fractions containing arylation product were pooled and concentrated to give compound 10 of at least 90% purity (according to 1H NMR analysis). It was used in the next step without further purification.

The synthetic route of 5164-76-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dar’In, Dmitry; Kantin, Grigory; Bakulina, Olga; ?alubovskis, Raivis; Krasavin, Mikhail; Synthesis; vol. 51; 10; (2019); p. 2230 – 2236;,
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Adding a certain compound to certain chemical reactions, such as: 21597-54-6, name is Methyl 3-amino-2-naphthoate, 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 21597-54-6, Product Details of 21597-54-6

Mix 5.0g (11.8mmol)12-bromo-10,10-dimethyl-10hydro-indeno[1,2-b]triphenylene(12-bromo-10,10-dimethyl-10H-indeno[1,2-b]triphenylene), 2.6 g (13.0 mmol) methyl 3-amino-2-naphthoate(methyl 3-amino-2-naphthoate),.13g (0.59 mmol) Pd(OAc)2, 0.17 g (0.59 mmol)Tri-tert-butylphosphonium tetrafluoroborate, 3.9 g (17.7 mmol) sodium tert-butoxide,80 ml of toluene was degassed and placed under nitrogen and then heated at 110 C for 16 h.After the reaction was completed, the mixture was allowed to cool to room temperature.The organic layer was extracted with dichloromethane and water and dried over anhydrous MgSO4.The solvent was removed and purified by silica gel column chromatography.The product was obtained (3.2 g, yield: 51%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-2-naphthoate, and friends who are interested can also refer to it.

Reference:
Patent; Jiguang Technology Co., Ltd.; Yan Fengwen; Deng Jinming; Zhuang Lijie; (80 pag.)CN107629068; (2018); A;,
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541-16-2, name is Di-tert-Butyl malonate, 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. Computed Properties of C11H20O4

Di-tert-butyl malonate (33.5 mL, 150 mmol) was added dropwise to a stirred suspension of NaH (6.0 g, 60 % suspension in oil, 150 mmol) in 1,2-dimethoxyethane (100 mL) under Ar, cooled in a water-ice bath. After stirring for 10 min, Intermediate 1G (16.2 g, 50 mmol) was added and the reaction was heated at 85 C for 20 h. After this time, acetic acid (100 mL) was added, the reaction flask was fitted with a distillation head and the temperature was raised to 130 C. 1,2-dimethoxyethane was distilled off under atmospheric pressure until the distillate was acidic (-100 mL). The distillation head was removed, a reflux condenser was attached, water (20 mL) was added and the reaction heated at 130 C for 12 h. The reaction was concentrated under reduced pressure and poured onto 200 g of ice and 100 mL of saturated aqueous NaOAc. Intermediate 1H was isolated as a white solid by filtration and further dried by reflxing with toluene in a Dean- Stark apparatus (11.0 g, 76 %). m/z ( +H)+= 288.2.1H- MR (400 MHz; DMSO-d6): delta 12.05 (bs, 1H), 8.79 (d, J= 4.5 Hz, 1H), 8.06 (dd, J= 9.2, 5.8 Hz, 1H), 7.94 (dd, J= 11.0, 2.8 Hz, 1H), 7.66-7.61 (m, 1H), 7.50 (d, J= 4.6 Hz, 1H), 2.41 (d, J= 7.6 Hz, 2H), 2.28- 2.23 (m, 1H), 1.87-1.78 (m, 2H), 1.73-1.64 (m, 6H).

The synthetic route of 541-16-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; CHERNEY, Emily Charlotte; SHAN, Weifang; WILLIAMS, David K.; ZHANG, Liping; (87 pag.)WO2019/74822; (2019); A1;,
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Application of 58656-98-7, These common heterocyclic compound, 58656-98-7, name is tert-Butyl 4-fluorobenzoate, 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.

tert-butyl 4-(4-hydroxy-4-phenylpiperidin-1-yl)benzoate A solution of 4-hydroxy-4-phenyl piperidine (221 mg, 1.25 mmol) in DMSO (1 mL) was treated with tert-butyl-4-fluorobenzoate (196 mg, 1.00 mmol) and powdered potassium carbonate (173 mg, 1.25 mmol), stirred vigorously at 125 C. for 16 hours, cooled to room temperature, diluted with diethyl ether, washed with brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (DCI(+)) m/e 354 (M+H)+.

Statistics shows that tert-Butyl 4-fluorobenzoate is playing an increasingly important role. we look forward to future research findings about 58656-98-7.

Reference:
Patent; Augeri, David J.; Baumeister, Steven A.; Bruncko, Milan; Dickman, Daniel A.; Ding, Hong; Dinges, Jurgen; Fesik, Stephen W.; Hajduk, Philip J.; Kunzer, Aaron R.; McClellan, William; Nettesheim, David G.; Oost, Thorsten; Petros, Andrew M.; Rosenberg, Saul H.; Shen, Wang; Thomas, Sheela A.; Wang, Xilu; Wendt, Michael D.; US2002/55631; (2002); A1;; ; Patent; Augeri, David J.; Baumeister, Steven A.; Bruncko, Milan; Dickman, Daniel A.; Ding, Hong; Dinges, Jurgen; Fesik, Stephen W.; Hajduk, Philip J.; Kunzer, Aaron R.; McClellan, William; Nettesheim, David G.; Oost, Thorsten; Petros, Andrew M.; Rosenberg, Saul H.; Shen, Wang; Thomas, Sheela A.; Wang, Xilu; Wendt, Michael D.; US2002/86887; (2002); A1;,
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Electric Literature of 75567-84-9, A common heterocyclic compound, 75567-84-9, name is Methyl 3-(4-bromophenyl)propanoate, molecular formula is C10H11BrO2, 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.

To a flask were added compound 50-6 (1.0 g, 3.5 mmol, the mixture of two trans isomers) , methyl 3- (4-bromophenyl) propionate (1.3 g, 5.3 mmol) , palladium acetate (100 mg, 0.445 mmol) , t-BuXPhos (300 mg, 0.63 mmol) , cesium carbonate (2.0 g, 6.1 mmol) and 1, 4-dioxane (10 mL) , the mixture was stirred at 90 for 3 hours and concentrated. The obtained residue was purified by silica gel column chromatography (PE/EA (V/V) = 1/1) to give the title compound as a white solid (1.0 g, 64%) . MS (ESI, pos. ion) m/z: 470.2 [M+Na] +.

The synthetic route of 75567-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Xinchang; REN, Qingyun; YAN, Guanghua; GOLDMANN, Siegfried; ZHANG, Yingjun; (253 pag.)WO2019/76310; (2019); 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., HPLC of Formula: C10H19BrO2

1h: Preparation of Compound 8 A 3-neck 300 mL round-bottomed flask equipped with a reflux condenser, magnetic stir bar and a nitrogen inlet was charged with 5 g (1 equivalent) of 4-hydroxybenzonitrile, absolute ethanol 150 mL, and 15.7 mL (1 equivalent) of sodium ethoxide. This mixture was stirred at 25 C. for 15 minutes. Ethyl 8-bromooctanoate (10.5 g, 1 equivalent) was then added dropwise over 10 minutes. The resulting mixture was heated to reflux (75 C.) for 72 hours. The reaction mixture was cooled and the solids filtered off. The solvent was removed on a rotary evaporator. The crude residue was dissolved in methylene chloride (200 mL) and washed with saturated NaHCO3 (2*75 mL), H2O (1*100 mL) and brine (1*100 mL). The crude material was then dissolved in ethanol (125 mL) and water (10 mL). LiOH (5 g) was added and the resulting mixture was heated to reflux (75 C.) for 1 hour then stirred at ambient temperature overnight. The solvent was evaporated and 75 mL of H2O was added. The aqueous solution was acidified to a pH of about 3 with concentrated HCl and the flask cooled to 4 C. An off-white colored solid precipitated. This material was collected by vacuum filtration and dried on the high vacuum overnight to give the crude acid. These solids were further purified by recrystallization from Ethyl acetate/hexanes (95/5) and again with chloroform to give 4.5 g of the product, 8-(4-cyanophenoxy)octanoic acid (41% yield). Melting point: 137-140 C. Molecular Formula: C15H19NO3. Combustion analysis: %C: 68.94 (calc’d), 68.57 (found); %H: 7.33(calc’d), 7.13(found); %N: 5.36 (calc’d), 5.28 (found).

The synthetic route of 29823-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Moye-Sherman, Destardi; Gschneidner, David; US2003/199427; (2003); A1;,
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Application of 50413-30-4,Some common heterocyclic compound, 50413-30-4, name is Methyl 2-amino-4-methoxylbenzoate, molecular formula is C9H11NO3, 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.

Referential Example 23 3.1 mL of triethylamine and 1.3 mL of benzoyl chloride were added to 19 mL of methylene chloride solution containing 1.9 g of methyl 2-amino-4-methoxybenzoate while ice-cooled sequentially and stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure and chloroform and 1.0 mol/L hydrochloric acid were added to the obtained residue. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue and a solid substance was separated by filtration to obtain 2.6 g of methyl 2-(benzamido)-4-methoxybenzoate as white solid. 1H-NMR (CDCl3) delta: 3.92 (3H, s), 3.93 (3H, s), 6.65 (1H, dd, J = 9.0, 2.7 Hz), 7.51-7.59 (3H, m), 8.00 (1H, d, H = 9.0 Hz), 8.05-8.07 (2H, m), 8.63 (1H, d, J = 2.7 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-amino-4-methoxylbenzoate, its application will become more common.

Reference:
Patent; TOYAMA CHEMICAL CO., LTD.; EP1820795; (2007); 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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Ethyl 3-(dimethylamino)acrylate

b) Ethyl 3-(dimethylamino)-2-(2-fluoro-4-acetoxybenzoyl)-2-propenoate A stirred solution of Intermediate 12a (4.91 g) in DCM (80 mL) was treated with oxalyl chloride (3.25 mL) and dimethylformamide (2 drops). After 2 h the clear solution was evaporated and re-evaporated from DCM (2x). The acid chloride was re-dissolved in toluene (100 mL) and treated with triethylamine (5.17 mL) and ethyl 3- (dimethylamino)acrylate (4.13 g). After stirring for 2 h at 9O0C the mixture was cooled, filtered and the solution flash chromatographed (silica gel 40 to 100% EtOAc in petroleum ether [b.p. 40-600C]) to give the title compound as a white solid (4.3 g); APCI m/z 324.0 [M+H]+.

The synthetic route of 924-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; PLIVA-ISTRAZIVACKI INSTITUT D.O.O.; WO2006/50942; (2006); A1;,
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Application of 150529-73-0, The chemical industry reduces the impact on the environment during synthesis 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, I believe this compound will play a more active role in future production and life.

Step 2: [00153] To a solution of the ester (6.0 g, 26.2 mmol) in tert-butanol (24 ml_) was added, under nitrogen atmosphere, sodium iodide (7.8 g, 52.4 mmol), N1N’- dimethylethylenediamine (0.3 ml_, 2.6 mmol) and copper iodide (0.3 g, 1.3 mmol). The reaction mixture was heated in a microwave apparatus at 145C for 1 h. Water (100 mL) was added and the product was extracted with ethyl acetate (3 x 50 mL). The organic layer was dried over sodium sulfate and concentrated. The residue was purified by flash chromatography on silica gel with a mixture of hexanes/ethyl acetate (8:2). This gave 3- iodophenylacetic acid methyl ester as a colorless oil (6.6 g, 86%). 1H NMR (400 MHz, CDCI3): d = 7.63 (m, 1 H), 7.58-7.61 (m, 1 H)1 7.23-7.26 (m, 1 H)1 7.05 (dd, J = 7.8 Hz, 1 H), 3.69 (s, 3H), 3.56 (s, 2H); LRMS (ESI): m/z = 277 (MH+).

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-(3-bromophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PROMETIC BIOSCIENCES INC.; ZACHARIE, Boulos; PENNEY, Christopher; GAGNON, Lyne; BIENVENU, Jean-Francois; PERRON, Valerie; GROUIX, Brigitte; WO2010/127440; (2010); A1;,
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