Tag: M.W=200-300

Reference of 6091-64-1, These common heterocyclic compound, 6091-64-1, name is Ethyl 2-bromobenzoate, 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.

Ethyl 2-bromobenzoate (1g, 4.37mmol) prepared from Step 1 wasdissolved in toluene (20 mL) and ethanol (4mL) mixed solution, and then theretowere added 4-fluorophenyl boronic acid (672mg, 4.80mmol), potassium carbonate(1.21g, 8.73mmol) and tetrakis (triphenylphosphine) palladium (504mg,0.44mmol). The reaction was stirred at 100 deg. C 6 hours, cooled to roomtemperature and filtered through Celite. The reaction was concentrated underreduced pressure to remove the solvent. Then washed with water and extracted ethyl acetate. Theorganic layer was dried over anhydrous magnesium sulfate, filtered andconcentrated. The resulting residue was purified by column chromatography toproduce the title compound (948mg, 89%).

Statistics shows that Ethyl 2-bromobenzoate is playing an increasingly important role. we look forward to future research findings about 6091-64-1.

Reference:
Patent; East Asia ST Corporation; Jin, Shunhui; Ren, Yuanbin; Cao, Zonghuan; Cui, Shangao; Pu, Zhengxiang; Jin, Miyan; Cui, Chenghe; Lee, Mingjing; Zhao, Kangxun; (182 pag.)CN105555761; (2016); A;,
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Related Products of 252881-74-6, 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. 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, This compound has unique chemical properties. The synthetic route is as follows.

[00229j Synthesis of N- [(PEG)3-COO-t-Buj -N?-Boc-N?-methyl-ethylene-diamine.To the solution of t-Bu-(PEG)3-amine (1 .01 g , 3.64 mmol) in 20 ml of methanol, (N-methyl)-N-Boc acetaldehyde(0.63 g, 3.64 mmol) was added. The mixture was stirred at room temperature for 3 hours. NaBH4 (0.412g, 10.9 mmol) was added to the mixture at 0C, and the resultant mixture was stirred at 0 C for 1 hour and 1 hour at room temperature. The reaction was quenched by adding 5 ml of water. After removal of solvent, 5 ml of water was added, and the mixture was extracted three times with methylene chloride. The combined organic layer was dried over Na2SO4, and the product was purified by flash silica chromatography using heptane/ethyl acetate to methylene chloride/methanol to give a yield of 72% (1.14 g). ?H NMR (300 MHz, CD2C12) oe ppm: 3.68 (t, 2H, OCH2), 3.56-3.60 (br, 1OH, CH2), 3.53 (t, 2H, OCH2), 3.29 (t, 2H, CH2), 2.85 (s, 3H, NCH3), 2.7-2.8 (m, 4H, NCH2), 2.47 (t, 2H, COCH2), 1.44 (s, 18H, CH3); MS-ESI (mle):435.5 [M+H].

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PROMEGA CORPORATION; MUSTAFA, Dana; ZHOU, Wenhui; MEISENHERMIER, Poncho; DUELLMAN, Sarah; MA, Dongping; CALI, James, J.; WO2015/116867; (2015); A1;,
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These common heterocyclic compound, 136333-97-6, name is Methyl 4-(2-bromoethyl)benzoate, 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. Computed Properties of C10H11BrO2

EXAMPLE 13({[(1Z)-2,2-Diethyl-1-oxidohydrazono]amino}oxy)methyl 4-{2-[({2-chloro-5-[(2-methyl-2,3-dihydro-1H-indol-1-yl)carbamoyl]phenyl}sulphonyl)amino]ethyl}benzoateStep A: Methyl 4-{2-[(tert-butoxycarbonyl)({2-chloro-5-[(2-methyl-2,3-dihydro-1H-indol-1-yl)carbamoyl]phenyl}sulphonyl)amino]ethyl}-benzoateDissolve the compound obtained in Step A of Example 1 (1.04×10-2 mol) in acetonitrile (20 ml) and place the solution under stirring. Add diisopropylethylamine (1.24×10-2 mol) and then, after stirring for 10 minutes, intermediate 9 (2.20×10-2 mol) dissolved in acetonitrile (20 ml). Heat the mixture at 60 C. After 5 days, the reaction mixture is evaporated to dryness under reduced pressure. The residue obtained is chromatographed on a silica column using as eluant a 75/25 n-heptane/ethyl acetate mixture.The title product is obtained in the form of a pale yellow meringue.

The synthetic route of Methyl 4-(2-bromoethyl)benzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LES LABORATOIRES SERVIER; US2010/286225; (2010); 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. 15848-22-3, name is 5-Bromopentyl acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 5-Bromopentyl acetate

1- (4-METHOXY-PHENYL)-3-TRIFLUOROMETHYL-1, 4,5, 6-tetrahydro- pyrazolo [3,4-c] pyridin-7-one (0.500 g, 1.606 mmol) was dissolved in N, N- DIMETHYLFORMAMIDE (20 mL) and cooled to 0 OC. Sodium hydride (60%, 0.161 g, 4.016 mmol) was added followed by 5-BROMOPENTYL acetate (0.535 mL, 3.213 MMOL). The reaction was stirred at rt overnight, quenched with IN hydrochloric acid (100 mL), EXTRACTED WITH ETHYL ACETATE (3100 ML), WASHED WITH WATER (2X1100 L), washed with brine (1X100 mL), dried over MGSO4, concentrated, and purified by flash CHROMATOGRAPHY USING 0-100% ETHYL ACETATE/HEXANES gradient as the eluent to afford 6- [1- (4-METHOXY-PHENYL)-7-OXO-3-TRIFLUOROMETHYL-1, 4,5, 7-TETRAHYDRO- pyrazolo [3, 4-c] pyridin-6-yl]-hexanoic acid methyl ester (0.699 g, 99%). The ester (0.800 g, 1. 82 mmol) was dissolved in tetrahydrofuran (40 mL), 1M lithium borohydride (3.64 ML, 3.64 mmol) was added, and the reaction was refluxed overnight. The reaction was quenched with water (150 mL), extracted with ethyl acetate (3X150 ML), washed with brine (1X150 mL), dried over MGSO4, concentrated, and purified by flash chromatography using 0-100% ethyl ACETATE/HEXANES as the eluent to afford 0.478 g (64%): 1H NMR (CDCl3) 8 7.44 (d, j=8. 8 Hz, 2H), 6.96 (d, j=9.2 Hz, 2H), 3.84 (s, 3H), 3.67 (t, j=6. 8 Hz, 2H), 3.61 (t, j=6. 4 Hz, 2H), 3.47 (t, j=7. 5 Hz, 2H), 3.00 (t, j=6. 8 Hz, 2H), 1.65-1. 50 (m, 4H), 1.45-1. 30 (m, 4H) ppm.

The synthetic route of 15848-22-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRYSTOL-MYERS SQUIBB COMPANY; WO2004/83177; (2004); A2;,
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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. 120-51-4, name is Benzyl benzoate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

General procedure: In a glove box, add a ruthenium complex Ia (0.3 to 0.7 mg, 0.0002 to 0.001 mmol) to a 300 mL autoclave,Potassium methoxide (35-700 mg, 0.5-10 mmol), tetrahydrofuran (4-60 mL), and ester compounds (10-200 mmol).After sealing the autoclave, take it out of the glove box and fill it with 50 100atm of hydrogen.The reaction kettle was heated and stirred in an oil bath at 100 C for 10 to 336 hours.After the reaction kettle was cooled in an ice-water bath for 1.5 hours, the excess hydrogen was slowly released.The solvent was removed from the reaction solution under reduced pressure, and the residue was purified with a short silica gel column to obtain an alcohol compound. The results are shown in Table 5.

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 120-51-4.

Reference:
Patent; Zhejiang Zhongke Chuangyue Pharmaceutical Co., Ltd.; Ding Kuiling; Tang Yitian; Han Zhaobin; (55 pag.)CN110357923; (2019); A;,
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Electric Literature of 1459-96-7,Some common heterocyclic compound, 1459-96-7, name is Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate, molecular formula is C12H18O4, 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.

At atmospheric conditions, 0.1 g of the Milstein catalyst precursor [2-(Di-tert- butylphosphinomethyl)-6- (0259) (diethylaminomethyl)pyridine]carbonylchlorohydridoruthenium(ll), 30 mg of potassium hydroxide, 2.5g of dimethyl bicyclo[2.2.2]octane-1 ,4-dicarboxylate and 50 imL of p- xylene were added to a 100 imL autoclave reactor. The reactor was then purged three times by pressurizing with nitrogen to 200 psig, then venting the pressure to atmospheric each time. The reactor was then purged three times by pressurizing with hydrogen to approximately 300 psig, then venting the pressure to atmospheric each time. Agitation at 800 rpm was then commenced, and hydrogen was then added to bring the pressure to 750 psig. The temperature was then increased to 140 C while allowing pressure to rise. After the temperature reaches 140 C, the hydrogen pressure was increased to 1000 psig. These conditions (140 C and 1000 psig) were held for 8 hours of reaction. After 8 hours of reaction, the agitation was stopped and the heat turned off to let the autoclave start cooling. After cooling to room temperature, pressure was released, and the contents were purged with nitrogen gas and vented. The solution was finally discharged from the autoclave and analyzed by GC-MS and 1H NMR. The conversion of dimethyl bicyclo[2.2.2]octane-1 ,4-dicarboxylate is 94%; the selectivity of bicyclo[2.2.2]octane-1 ,4-diyldimethanol is 93%; and the selectivity of methyl 4-(hydroxymethyl)bicyclo[2.2.2]octane-1 -carboxylate is 7%.

The synthetic route of 1459-96-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EASTMAN CHEMICAL COMPANY; HU, Yue, Rachel; HEMBRE, Robert, Thomas; TUSTIN, Gerald, Charles; LIU, Zhufang; ADAMS, Steven, J.; CLARKSON, Jasper, Randle; (59 pag.)WO2019/75004; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, 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 252881-74-6, HPLC of Formula: C13H27NO5

To 13-amino-4, 7, 10-trioxadodecanoic acid tert-butyl ester (0.80 g, 2.89 mmol) in 30 mL of dioxane was 10 ml of HCl (36%) with stirring. After 0.5 h TLC analysis revealed that the reaction was complete, the reaction mixture was evaporated, and co-evaporated with EtOH and EtOH/Toluene to form the title product in HCl salt (>90%pure, 0.640 g, 86%yield) without further purification. ESI MS m/z+ C 9H 20NO 5 (M+H) , cacld. 222.12, found 222.20.

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:
Patent; HANGZHOU DAC BIOTECH CO., LTD; ZHAO, Robert Yongxin; ZHUO, Xiaotao; YANG, Qingliang; ZHAO, Linyao; HUANG, Yuanyuan; YE, Hangbo; YANG, Chengyu; LEI, Jun; GAI, Shun; GUO, Huihui; JIA, Junxiang; BAI, Lu; XIE, Hongsheng; ZHOU, Xiaomai; GUO, Zhixiang; LI, Wenjun; CAO, Mingjun; ZHENG, Jun; YE, Zhichang; YANG, Yanlei; (325 pag.)WO2020/6722; (2020); A1;,
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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. 33155-58-7, name is tert-Butyl 2-(4-Bromophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

To a stirring solution of 2-(5-chlorothiophen-2-yl)-4-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (1 eq.)in toluene (1.5 ml) was added Na01Bu (1.6 eq.), tert-butyl 2-(4-bromophenyl)acetate (1.5eq.) and BINAP (0.04 eq.). The resulting reaction mixture was degassed with argon for a period of 10 min. and Pd2dba3 (0.02eq.) was added and the mixture was degassed again. The reaction mixture was heated at 100C for16 h. At completion, the reaction mixture was concentrated and poured in DMF (2 mi).The inorganics were filtered and the residue was purified by prep-HPLC using aqueous ammonia method to give tert- butyl 2-(4-(2-(5-chlorothiophen-2-yl)-4-methyi-5H-pyrrolo[2,3-d]pyrimidin-7(6H)-yl)phenyl)acetate which was directly used for the next step. ).

According to the analysis of related databases, 33155-58-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUeNENTHAL GMBH; JAKOB, Florian; KONETZKI, Ingo; CRAAN, Tobias; NARDI, Antonio; HESSLINGER, Christian; WO2015/18534; (2015); A1;,
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15964-79-1, name is Methyl 2-(3,4-dimethoxyphenyl)acetate, 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. COA of Formula: C11H14O4

6,7-Dimethoxy-1-methylisoquinolin-3-ol CCH 18060 To a solution of methyl 2-(3,4-dimethoxyphenyl)acetate SLA 28134 (23.82 g, 113.30 mmol) in acetic anhydride (57 mL) at 0 C. in a 1 L round-bottomed flask equipped with a magnetic stirrer under N2 was added perchloric acid (70% solution in water, 11.3 mL) over a period of 30 min. The reaction mixture was then allowed to warm up to RT, stirred for a further 45 min and diluted with Et2O (450 mL). The solid was then filtered and washed several times with Et2O (6*15 mL) to give after drying under vacuum a dark yellow solid (27.97 g, 74% yield). To a suspension of the above solid (11.09 g, 34.58 mmol) in H2O (60 mL) in a 500 mL 3-neck round-bottomed flask equipped with a dropping funnel and a magnetic stirrer in an ice bath was added dropwise conc. NH4OH (90 mL) and the reaction mixture was stirred at RT for 1 h, after which the solid was filtered and washed with cold water (4*15 mL). After drying under high vacuum, 6,7-dimethoxy-1-methylisoquinolin-3-ol CCH 18060 was isolated as a yellow solid (7.53 g, 99% yield). MW: 219.24; Yield: 74%; Yellow solid; Mp ( C.): 283 (dec.). Rf: 0.2 (cyclohexane:EtOAc=2:1). 1H-NMR (DMSO d6, delta): 2.68 (s, 3H, CH3), 3.85 (s, 3H, OCH3), 3.86 (s, 3H, OCH3), 6.51 (s, 1H, ArH), 6.97 (s, 1H, ArH), 7.12 (s, 1H, ArH), 10.69 (broad s, 1H, OH). 13C-NMR (DMSO d6, delta): 20.3, 55.6, 55.7, 99.5, 103.6, 103.8, 116.2, 138.0, 147.1, 152.0, 153.3, 159.0. MS-ESI m/z (rel. int.): 220 ([M+H]+, 100).

The synthetic route of 15964-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ExonHit Therapeutics SA; ALLERGAN, INC.; US2012/214837; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1186-73-8, name is Trimethyl methanetricarboxylate, 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 1186-73-8, Safety of Trimethyl methanetricarboxylate

N-benzyl-3-isopropyl-7-methoxy-6-(3-methoxypropoxy)tetralin-1-imine (1 g, 2.53 mmol) and trimethyl methanetricarboxylate (1.44 g, 7.6 mmol) were dissolved in diglyme (10 mL). The reaction mixture was stirred at 180 C in a microwave reactor for 30 minutes. Ethyl acetate (20 mL), followed by H2O (30 mL) were added to the reaction mixture. The separated organic layer was washed with H2O (2 x 20 mL), saturated aqueous brine solution (2 x 20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by normal phase SiO2; chromatography (0 to 70 % EtO Ac/hexanes) to give methyl 1-benzyl-4-hydroxy-5-isopropyl-9-methoxy-8-(3-methoxypropoxy)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carboxylate as a yellow oil (560 mg, 42% yield, m/z: 522 [M+H] observed).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Trimethyl methanetricarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ARBUTUS BIOPHARMA, INC.; CHEN, Shuai; DORSEY, Bruce D.; FAN, Yi; GOTCHEV, Dimitar B.; QUINTERO, Jorge; (252 pag.)WO2019/177937; (2019); A1;,
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