Month: August 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. 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, A new synthetic method of this compound is introduced below., COA of Formula: C18H21NO4

General procedure: The corresponding N-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl-oxycarbonyl) amino acids 20a-h (0.47 mmol) were dissolved in 50 mL of anhydrous CH2Cl2 and cooled to 0 C. 1-Hydroxybenzotriazole (HOBt) (0.7 mmol) and EDCI (0.56 mmol) were added, and the mixture was stirred for 30 min at 0 C. Subsequently, 0.39 mmol of compound 3 and finally 2.4 mL of N-ethyl diisopropylamine were added. The mixture was stirred for 16 h at ambient temperature. The solvent was removed under reduced pressure and the residue was purified by flask-column chromatography (gradient elution with mixtures of chloroform/methanol) on silica gel as monitored by TLC. Synthesized target compounds 21a-h were characterized by mp, IR, ESR and HRMS analyses.

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:
Article; Liu, Ying-Qian; Li, Xiao-Jing; Zhao, Chun-Yan; Nan, Xiang; Tian, Jing; Morris-Natschke, Susan L.; Zhang, Zhi-Jun; Yang, Xiao-Ming; Yang, Liu; Li, Lin-Hai; Zhou, Xing-Wen; Lee, Kuo-Hsiung; Bioorganic and Medicinal Chemistry; vol. 21; 5; (2013); p. 1248 – 1256;,
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Reference of 41365-75-7,Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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.

General procedure: To a solution of 2.05 g (14 mmol) of 3,3-diethoxypropan-1-amine 3 and 2.83 g (28 mmol) of triethylamine in 15 ml of benzene 14 mmol of N,N-di(alkyl, aryl)carbamoyl chloride was added dropwise at cooling (5-7 C). The reaction mixture was stirred under cooling for 2 hours. The precipitate was filtered off, the filtrate was evaporated in vacuum to give the target compound 4 as a yellow oil, which was used in subsequent reactions without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Amino-3,3-diethoxypropane, its application will become more common.

Reference:
Article; Smolobochkin, Andrey V.; Gazizov, Almir S.; Burilov, Alexander R.; Pudovik, Michail A.; Synthetic Communications; vol. 48; 19; (2018); p. 2545 – 2552;,
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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. 1484-26-0, name is 3-Benzyloxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 1484-26-0

3-Benzyloxyaniline (80 mg, 0.40 mmol) was dissolved in DCM and cooled to 0 °C. Bromoacetyl bromide (2 equiv, 70 lL) and Et3N (5 equiv, 280 lL) were added slowly and the mixture was stirred at 0 °C for 6 h. 2,5-Dimethoxybenzylamine (2.5 equiv, 151 lL)was added at 0 °C and the mixture was allowed to warm over 16 h of stirring. Boc2O (6 equiv, 524 mg) was added along with 2 addition equiv of Et3N and DMAP (0.2 equiv, 10 mg) and the mixture was stirred for 1 h at rt. The reaction mixture was diluted with satd NaHCO3 and extracted with DCM. The crude product was purified by pTLC with 30percent EtOAc in hexane to afford N-Boc-33 as a colorlessoil (49 mg, 24percent).

The synthetic route of 1484-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bremer, Paul T.; Hixon, Mark S.; Janda, Kim D.; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 3971 – 3981;,
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Synthetic Route of 929-75-9,Some common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, 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.

General procedure: A mixture of 3,4-dihydroxycinnamic acid (497mg, 2.76mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI) (794mg, 4.14mmol), 1-hydroxybenzotriazole (HOBt) (559mg, 4.14mmol), Et3N (0.58mL, 4.14mmol) in anhydrous DMF (10mL) was stirred under an atmosphere of argon for 10minat 26C. Propane-1,3-diamine (102mg, 1.38mmol) was added, and the mixture was stirred for 18hat 26C. The mixture was concentrated under reduced pressure to give a crude coupling product of the title compound (2). To facilitate isolation, the coupling product was treated with Ac2O (10mL) in pyridine (10mL) at 26C for 12h. The mixture was concentrated, and extracted with EtOAc and water for three times. The organic layers were combined and washed with water (10mL) and brine (10mL). The organic phase was dried over MgSO4, filtered, concentrated, and purified by silica gel chromatography (EtOAc elution) to afford the acetylation compound. To a solution of the acetylation compound in MeOH (10mL) was added K2CO3 (13mg, 0.13mmol). The mixture was stirred for 0.5hat 26C, and then acidified to pH 5 by addition of Dowex 50WX8-200 cationic exchange resin. The resin was then removed by filtration. The filtrate was concentrated, and purified by silica gel chromatography (EtOAc, then MeOH/CH2Cl2 1:4) to give pure compound 2 (146mg, 27% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,11-Diamino-3,6,9-trioxaundecane, its application will become more common.

Reference:
Article; Tu, Ling-Hsien; Tseng, Ning-Hsuan; Tsai, Ya-Ru; Lin, Tien-Wei; Lo, Yi-Wei; Charng, Jien-Lin; Hsu, Hua-Ting; Chen, Yu-Sheng; Chen, Rong-Jie; Wu, Ying-Ta; Chan, Yi-Tsu; Chen, Chang-Shi; Fang, Jim-Min; Chen, Yun-Ru; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 393 – 404;,
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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. 366-99-4, name is 3-Fluoro-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., name: 3-Fluoro-4-methoxyaniline

3-Fluoro-4-methoxyaniline (1, R1 = H, R2 = CH3, R3 = F) (95 g, 0.67 mol) was added to concentrated hydrochloric acid (250 mL), the suspension was stirred at ambient temperature for 18 hours, then it was cooled to 0 0C and a solution of sodium nitrite (53.7 g, 0.78 mol) in water (200 mL) was added dropwise at 0-5 0C. When the addition was complete, the resulting solution was stirred at 0 0C for 1 hour then it was added dropwise at 0-5 0C to a stirred solution of tin (II) chloride dihydrate (638.9 g, 2.83 mol) in concentrated hydrochloric acid (500 mL). The mixture was allowed to warm to ambient temperature then it was stored at 4 0C for 18 hours. The resulting precipitate was collected by filtration, washed with water (400 mL), and ether (1000 mL) and dried in vacuo. The solid hydrochloride salt was basifed by addition to 10percent aqueous sodium hydroxide solution (800 mL), the free base was extracted into ether (2 X 400 mL), and the combined extracts were dried (MgSO4) and the solvent removed in vacuo to give (3- fluoro-4-methoxyphenyl)hydrazine (2, R1 = H, R2 = CH3, R3 = F) (51.9 g, 50percent) as a yellow solid, mp 46-50 0C; 1HNMR (CDC13/25O MHz): 1.5 (s, IH, NH-NH2), 3.85 (s, 3H, OCH5), 5.0 (s, 2Eta, NH-NH2), 6.44 (m, 1Eta, phenyl 6-H), 6.60 (dd, 1Eta, phenyl 5-H), 6.79 (t, 1Eta, phenyl 2-H)-

According to the analysis of related databases, 366-99-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MICROBIA, INC.; WO2007/22501; (2007); A2;,
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150-78-7, name is 1,4-Dimethoxybenzene, belongs to ethers-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. HPLC of Formula: C8H10O2

Example 1 : Preparation of 2,5-dimethoxybromobenzene (1); [00101] In a one liter round-bottom flask, a solution of bromine (16.0 g, 100 mmol) in acetic acid (50 ml) was added dropwise to a solution of 1 ,4- dimethoxybenzene (13.8 g, 100 mmol) in chloroform and methanol (400 ml) at 00C. After stirring for 3 hours, 500 ml of saturated Na2CO3 solution was added. The organic layer was washed with water, brine and dried over sodium sulfate. After the solvent was removed on a rotary evaporator, the residue was distilled under reduced pressure to yield 15.8 g of 2,5- dimethoxybromobenzene (yield 73%) 1HNMR (CDCI3) 57.148 (s, 1 H), 6.859 EPO (s, 2 H), 3.869 (s, 3 H), 3.785 (s, 3 H).

The synthetic route of 150-78-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NATIONAL UNIVERSITY OF SINGAPORE; WO2006/93467; (2006); A1;,
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Reference of 116557-46-1, These common heterocyclic compound, 116557-46-1, name is 3-Bromo-2-methoxyaniline, 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.

[00163] Intermediate 9B. (3-Bromo-2-methoxyphenyl)hydrazine: A suspension of Intermediate 9A (4.0 g, 20 mmol) in 6 M HC1 was cooled to -10 C and a solution of sodium nitrite (1.41 g, 20.8 mmol) in water (5 mL) was added slowly to keep the temperature below 0 C. After the addition, the reaction was stirred for additional 20 min at -10 C. A solution of tin (II) chloride (11.26 g, 59.39 mmol) in cone. HC1 (20 mL) was added slowly, resulting in precipitation. After 30 min, the precipitate was filtered, washed with cone. HC1 and then water, suspended in 10% NaOH solution, and extracted with EtOAc. The combined organics were dried over MgS04, filtered, and evaporated to give Intermediate 9B (1.8 g, 42%), which was used directly in the next step. LCMS (ESI) m/z 200, 202 (M-NH3+H, M-NH3+2+H)+, RT = 1.09 min (Method A).

The synthetic route of 116557-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; L’HEUREUX, Alexandre; HIEBERT, Sheldon; HU, Carol; LAM, Patrick Y.S.; LLOYD, John; PI, Zulan; QIAO, Jennifer X.; THIBEAULT, Carl; TORA, George O.; YANG, Wu; WANG, Yufeng; WANG, Tammy C.; BOWSHER, Michael S.; RUEL, Rejean; WO2014/22343; (2014); 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 102-52-3 as follows. SDS of cas: 102-52-3

ethyl 2-aminopyrazolo[l ,5-a]pyrimidine-3-carboxylateA mixture of ethyl 3,5-diamino-l H-pyrazole-4-carboxylate (1.0 g, 5.9 mmol), 1,1,3,3- tetramethoxypropane (2.9 mL, 18 mmol), triethylamine (2 mL, 10 mmol), and DMF (15 mL) was heated at 100 0C for 14 hrs, then a further 2 mL of 1,1,3,3-tetramethoxypropane was added. After adding the additional 1,1,3,3-tetramethoxypropane, a significant by-product was noted and heating was stopped immediately. The reaction was cooled to room temperature and the DMF was removed in vacuo. The residue was partitioned between DCM and water, then the organic layer was concentrated and the residue purified by silica chromatography, eluting with 95:5 DCM: 2M methanolic ammonia solution to afford 420 mg (35%) of ethyl 2-aminopyrazolo[l,5- a]pyrimidine-3-carboxylate. 1H NMR (500 MHz, CDCl3) delta 8.57 (dd, J = 4.3, 1.6, IH), 8.43 (dd, J = 6.7, 1.6, IH), 6.84 (dd, J = 6.7, 4.4, IH), 5.52 (s, 2H), 4.48 (q, J= 7.1, 2H), 1.45 (t, J= 7.1, 3H).

According to the analysis of related databases, 102-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; GIBBONS, Paul; HANAN, Emily; LIU, Wendy; LYSSIKATOS, Joseph P.; MAGNUSON, Steven R.; MENDONCA, Rohan; PASTOR, Richard; RAWSON, Thomas E.; SIU, Michael; ZAK, Mark E.; ZHOU, Aihe; ZHU, Bing-Yan; WO2011/3065; (2011); A2;,
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Reference of 38380-85-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 38380-85-7 name is 1-Bromo-4-cyclopropoxybenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 1: 1-bromo-4-(cyclopropyloxy)benzene (9.5 g, 45 mmol), DMA (66 mL), and MeOH (33 mL) were added to a bomb reactor and degassed by bubbling through argon for 5 minutes. The degassed mixture was charged with DPPF (1.85 g, 3.34 mmol) and Pd(OAc)2 (0.50 g, 2.2 mmol) and degassed under CO. The reaction was heated in the bomb at 15 psi CO at 80C for 18 h. The crude reaction mixture was filtered through celite and concentrated under reducedpressure. The residue was purified by column chromatography on silica gel (5 – 25% EtOAc/hexane) to afford methyl 4-cyclopropoxybenzoate.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-cyclopropoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; FISCHER, Christian; BOGEN, Stephane, L.; CHILDERS, Matthew, L.; LLINAS, Francesc Xavier Fradera; ELLIS, J. Michael; ESPOSITE, Sara; HONG, Qingmei; HUANG, Chunhui; KIM, Alexander, J.; LAMPE, John, W.; MACHACEK, Michelle, R.; MCMASTERS, Daniel, R.; OTTE, Ryan, D.; PARKER, Dann, L., Jr.; REUTERSHAN, Michael; SCIAMMETTA, Nunzio; SHAO, Pengcheng, P.; SLOMAN, David, L.; UJJAINWALLA, Feroze; WHITE, Catherine; WU, Zhicai; YU, Yang; ZHAO, Kake; GIBEAU, Craig; BIFTU, Tesfaye; BIJU, Purakkattle; CHEN, Lei; CLOSE, Joshua; FULLER, Peter, H.; HUANG, Xianhai; PARK, Min, K.; SIMOV, Vladimir; WITTER, David, J.; ZHANG, Hongjun; (297 pag.)WO2016/89797; (2016); A1;,
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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. 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H7F3N2O

N1-pyrrolidine cyanoguanidine (72 mg, 0.52 mmol) and 4-trifluoro methoxy phenylene diamine (0.1 g, 0.52 mmol) were dissolved in distilled water (10 ml) at room temperature, and then hydrochloric acid(0.1 ml, 1.04 mmol) was added thereto, and stirred with reflux at 110 C. for 2 hr. The reaction mixture was added by 10% potassium hydroxide solution, and then the obtained solid was filtrated under reduced pressure, and was washed with distilled water. The filtrated solid was dried under reduced pressure. The title compound was produced in brown solid phase(20 mg, 12.2%). 1H NMR (600 MHz, CD3OD) delta 7.22 (d, J=8.4 Hz, 1H), 7.13 (s, 1H), 6.90 (d, J=8.4 Hz, 1H), 3.49 (br s, 4H), 1.92 (s, 4H); LC-MS m/z 235.1 [M+1]

According to the analysis of related databases, 658-89-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HANALL BIOPHARMA CO., LTD.; KIM, Hong Woo; LEE, Ji Sun; HEO, Hye Jin; LEE, Hong Bum; JEONG, Jae Kap; PARK, Ji Hyun; KIM, Seo-il; LEE, Young Woo; US2015/126518; (2015); A1;,
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