Month: September 2021

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. 49851-36-7, name is Methyl 2-(2-aminophenyl)acetate hydrochloride, A new synthetic method of this compound is introduced below., Quality Control of Methyl 2-(2-aminophenyl)acetate hydrochloride

To a solution of methyl 2-(2-aminophenyl)acetate hydrochloride (CAS 49851-36-7) (0.50 g, 2.5 mmol) in DMF (24.8 ml) at 0 C was added NBS (0.441 g, 2.48 mmol) and this was stirred at 0 C. After 10 minutes the reaction was quenched with saturated aqueous sodium bicarbonate, extracted with EtOAc, washed with water, dried over MgS04, filtered and concentrated. This was purified by flash chromatography (0-15% EtOAc:DCM) to provide the title compound. MS (ESI+) m/z 244.1 , 246.1 (M+H).

The synthetic route of 49851-36-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BELANGER, David B.; FLOHR, Stefanie; GELIN, Christine Fang; JENDZA, Keith; JI, Nan; LIU, Donglei; LORTHIOIS, Edwige Liliane Jeanne; KARKI, Rajeshri Ganesh; MAINOLFI, Nello; POWERS, James J.; RANDL, Stefan Andreas; ROGEL, Olivier; VULPETTI, Anna; YOON, Taeyoung; WO2015/9977; (2015); A1;,
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Electric Literature of 18448-47-0, 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. 18448-47-0, name is Methyl cyclohex-1-enecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Cyclohex-l-en-l-ylmethanol To a solution of methyl 1-cyclohexene-l-carboxylate (1.50 mL, 11.0 mmol) in DCM (30 mL) was added diisobutylaluminum hydride (1M solution in toluene; 25 mL, 25 mmol) at -78 C and the mixture was stirred for 1 h. TLC (3:1 hex:EtOAc) showed that the reaction was then complete. The mixture was quenched with methanol (10 mL) and IN NaOH (10 mL) and then was allowed to stir at rt for 2.5 h. The mixture was extracted with DCM (3x). The combined organic layers were washed with brine, dried over MgSCt, filtered and concentrated to give cyclohex-l-en-l-ylmethanol (1.3 g, 100%).

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 cyclohex-1-enecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; DUFFEY, Matthew, O.; ENGLAND, Dylan, B.; HU, Zhigen; ITO, Mitsuhiro; LANGSTON, Steven, P.; MCINTYRE, Charles; MIZUTANI, Hirotake; XU, He; WO2015/2994; (2015); A2;,
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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 139102-34-4 as follows. Quality Control of Methyl 4-bromo-2-methoxybenzoate

A solution of 4-bromo-2-methoxybenzoic acid methyl ester (0.1 mol) and tetrahydro- 2H”-pyran-4-amine (0.3 mol) in 1 -methyl-2-pyrrolidinone (800 ml) was stirred at 400C. Cs2CO3 (0.2 mol) was added. The reaction mixture was stirred for 5 minutes. Pd2(dba)3 (0.002 mol) and BINAP (0.003 mol) were added. The reaction solution was degassed by applying alternating nitrogen atmosphere and vacuum. The reaction mixture was stirred overnight at 110C. The 1 -methyl-2-pyrrolidinone solvent was evaporated. The residue was purified by high-performance liquid chromatography. The product fractions were collected and the solvent was evaporated, yielding 13 g of intermediate (29).

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; JANSSEN PHARMACEUTICA NV; WO2009/62990; (2009); A2;,
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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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Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics