Month: July 2021

Synthetic Route of 36805-97-7,Some common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, 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.

1 , 1-Di-te/f-butoxy-A/,A/-dimethylmethanamine (6.77 ml, 28.3 mmol) was added to a suspension of 2-({[(benzyloxy)carbonyl]amino}methyl)-1-ethyl-1 /-/-1 ,3-benzodiazole-6- carboxylic acid, Intermediate 80 (2.50 g, 7.08 mmol) in alpha,alpha,alpha-trifluorotoluene (50 ml). The reaction mixture was heated at 100 C for 1 h. The reaction mixture was allowed to cool to RT then 1 , 1-di-te/f-butoxy-A/,A/-dimethylmethanamine (6.77 ml, 28.3 mmol) was added dropwise over 15 min. The resultant mixture was heated at 100 C for 45 min. The reaction mixture was cooled to 50 C then 1 , 1-di-te/f-butoxy-A/,A/-dimethylmethanamine (3.38 ml, 14.15 mmol) was added dropwise over 5 min. The resultant mixture was heated at 100C for 0.5 h then allowed to cool to RT. The reaction mixture was partitioned between EtOAc (50 ml) and water (50 ml). The phases were separated then the organic phase was washed with water (2 x 30 ml), saturated aqueous NaHCC solution (20 ml) and brine (10 ml) then dried over Na2S04, filtered and concentrated in vacuo to afford a beige solid (2.5 g). The solid thus obtained was suspended in MeCN (10 ml). The solid was collected by filtration then dried under vacuum to afford the product as an off-white solid (2.30 g, 79%). 1 H NMR (500 MHz, DMSO-cfe) delta 8.07 (s, 1 H), 7.97 (m, 1 H), 7.76 (dd, J = 8.4, 1.5 Hz, 1 H), 7.64 (d, J = 8.4 Hz, 1 H), 7.34 (m, 5H), 5.07 (s, 2H), 4.55 (d, J = 6.0 Hz, 2H), 4.38 – 4.25 (m, 2H), 1.57 (s, 9H), 1.29 (m, 3H). LC/MS (System A): m/z (ESI+) = 410 [MH+], Rt = 1.17 min, UV purity = 99%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, its application will become more common.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan, David; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; WENT, Naomi; (261 pag.)WO2018/96325; (2018); A1;,
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Reference of 17715-69-4, A common heterocyclic compound, 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, molecular formula is C8H9BrO2, 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.

A thermometer, a stirrer, a reflux condenser attached to the flask, and subjected to nitrogen gas purging, 1-bromo-2,4-dimethoxybenzene 110g, 257g IPA, and potassium carbonate added to the solution previously prepared by dissolving 139g to 107g water and the reaction vessel was stirred while nitrogen It is replaced, and then tetrakistriphenylphosphine palladium (0), adding to 5.9g, also 4-methoxy-phenylboronic acid to pre-IPA 109g 83g Solution was added dropwise to the dissolved. After 3 hours the reaction mixture was heated to reflux, added 500mL of water, separate the IPA layer, the water layer was Transferred to a separatory funnel, the toluene extract was added 500mL. An organic layer was washed with saturated sodium chloride solution each. Solvents in vacuo After distilling off the one, added 500mL of toluene, and the precipitate was separated by filtration, toluene was distilled off under reduced pressure. Methane to the obtained crude product Adding to come 200mL, taking over the precipitate, and dried 5 hours in a vacuum dryer of 50 , 2,4,4′- tree fertilization methoxy phenyl Gained 105g

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:
Patent; Dainippon Inc. & Chemicals; Yoshimoto, Yasuyo; Morinika, Kunihiro; Kinoshita, Hiroshi; (17 pag.)KR2016/8529; (2016); A;,
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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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, A new synthetic method of this compound is introduced below., name: 4-(Difluoromethoxy)aniline

In tetrahydrofuran (10 ml) was dissolved 4-difluoromethoxyaniline (1 .0 g 6.29 mmol). To this, pyridine (1 .0 ml, 12.58 mmol) and methane sulfonyl chloride (0.7 ml, 9.43 mmol) were added at 0-5 C and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with water and brine solution. Organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude product (1 .5 g) was used as such for next step. 1 H-NMR(400MHz,DMSO-d6)delta: 2.97(s,3H),7.16(d,J=8.8Hz,2H),7.16(t,J=7.4Hz, 1 H), 7.24 (d,J=9.2Hz,2H),9.77(s,1 H).

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; KATOCH, Rita; INAGAKI, Hiroaki; FUJISAWA, Tetsunori; WO2014/24056; (2014); A1;,
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Reference of 5905-69-1, A common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, molecular formula is C7H5BrF2O, 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 stirred solution of bromophenol derivative AM (2.0 g, 8.97 mmol) in 1,4-dioxane (40 mL) were added bis(pinacolato)diboron (2.28 g, 8.97 mmol) and KOAc (2.64 g, 26.90 mmol) at RT under inert atmosphere, and the mixture was degassed for 20 min by purging with argon. To this solution, Pd(dppf)2Cl2 (0.33 g, 0.45 mmol) was added, and the mixture was degassed for a further 10 min. The reaction mixture was then heated to 80 C. and stirred for 3 h at this temperature. Progress of the reaction was monitored by TLC. The reaction mixture was then cooled to RT and diluted with EtOAc (30 mL). The resultant solution was filtered through a Celite pad, and the filtrate was then concentrated in vacuo. The crude compound was purified by silica gel column chromatography (eluting with 5-10% EtOAc gradient in hexanes) to afford AN (1.72 g, 6.37 mmol, 71%). 1H NMR (500 MHz, CDCl3): delta 7.81 (d, J=8.5 Hz, 2H), 7.09 (d, J=8.5 Hz, 2H), 6.54 (t, JF-H=74.0 Hz, 1H), 1.34 (s, 12H).

The synthetic route of 5905-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIAMET PHARMACEUTICALS, INC.; US2012/329802; (2012); A1;,
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Application of 126829-31-0, A common heterocyclic compound, 126829-31-0, name is 2-Ethynyl-1,3-dimethoxybenzene, molecular formula is C10H10O2, 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.

General procedure: The arylalkyne 1,acetic anhydride (Ac2O), and an anhydrous solvent were added to a dried three-necked flask under argon atmosphere and the mixture was stirred for 30 min at room temperature. Further, HCl(g)prepared using H2SO4 and NaCl at 160 8C was added to the mixture through the rubber tube until the starting material conversed completely, monitored by TLC, and the unreacted HCl(g) was absorbed by aqueous NaOH. The solvent was removed and the residue was purified using flash chromatography on a silica gel.

The synthetic route of 126829-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xu, Cai-Xia; Ma, Cun-Hua; Xiao, Fu-Rong; Chen, Hong-Wei; Dai, Bin; Chinese Chemical Letters; vol. 27; 11; (2016); p. 1683 – 1685;,
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Related Products of 262587-05-3, 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. 262587-05-3, name is 1-Bromo-3-(difluoromethoxy)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a flask containing 1-bromo-3-(difluoromethoxy)benzene (350 mg, 1.58 mmol) and 1,4-dioxa-8-azaspiro[4.5]decane (249 mg, 1.74 mmol) in dioxane (10 mL) was added t-BuONa (303mg, 3.16 mmol), under N2 After being heated with stuffing at 100 C overnight, the resulting reaction mixture was cooled to rt, diluted with H20 (30 mL) and extracted with EA (30 mL) for three times. The combined organic layer was washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give 8-[3-(difluoromethoxy)phenyl]-1,4-dioxa-8-azaspiro[4.5]decane (450 mg), which was used in the next step without further purification.

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, 1-Bromo-3-(difluoromethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Bromo-4-fluoro-2-methoxybenzene

A total of 716 mg of aluminium chloride was suspended in 24.4 ml of dichloromethane and was then mixed with 0.65 ml of 3-fluorobenzoyl chloride and 1 g of 1-bromo-4-fluoro-2-methoxy-benzene obtained in Production Example II-1-a under stirring at -60C. The mixture was raised in temperature to room temperature over 2.5 hours and was stirred for further 3 hours. Water was added to the reaction mixture under ice-cooling, followed by extracting with diethyl ether. The resulting organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine, dried over magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane = 1:10), to give 856 mg of the title compound as white crystals.1H-NMR ( 400 MHz, CDCl3 ) d 3.98 ( 3H, s ), 6.69 ( 1H, d, J = 11.6 Hz ), 7.27 – 7.58 ( 4H, m ), 7.83 ( 1H, d, J = 7.2 Hz )

According to the analysis of related databases, 450-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eisai Co., Ltd.; EP1380576; (2004); A1;,
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Related Products of 54149-17-6, The chemical industry reduces the impact on the environment during synthesis 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, I believe this compound will play a more active role in future production and life.

Example 48 Preparation of N-{5-[2-(2-methoxyethoxy)ethoxy]pyridin-3-yl}-17-methylmorphinan-3- amine (48), hydrochloride salt Step 1. Synthesis of 3-bromo-5-(2-(2-methoxyethoxy)ethoxy)pyridine, A mixture of 5-bromopyridin-3-ol (100 mg, 0.575 mmol), l-bromo-2-(2- methoxyethoxy)ethane (105 mg, 0.575 mmol) and K2C03 (159 mg, 1.149 mmol) in DMF (3 mL) was irradiated in a microwave at 80 C for two hours. The reaction mixture was cooled to room temperature and poured into 15 mL of ethyl acetate and IN NaOH (20 mL). The organic layer was washed with brine (20 mL), dried over anhydrous sodium sulfate, was filtered and was concentrated. The crude product was purified by flash column chromatography on silica gel to afford 3-bromo-5-(2-(2-methoxyethoxy)ethoxy)pyridine (82.7 mg, 52.1%). MS (EI) for Ci0Hi4BrNO3: 277.8 (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, 1-Bromo-2-(2-methoxyethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEKTAR THERAPEUTICS; ANAND, Neel; AURRECOECHEA, Natalia; CHENG, Lin; DENG, Bo-liang; O’MAHONY, Donogh; MU, Yongqi; KROGH-JESPERSEN, Erik; (215 pag.)WO2016/182840; (2016); A1;,
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Application of 171290-52-1,Some common heterocyclic compound, 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, molecular formula is C10H10O2, 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 solution of methoxy ethynylbenzenes (20 mmol) and methoxy substituted aryl iodide (22 mmol) in isopropylamine (120 ml) were added Pd(PPH3)2Cl2 (0.2 mmol) and CuI (0.4 mmol). The reaction mixture was stirred at ambient temperature for 6 hours under a slow stream of nitrogen. The reaction mixture was filtered and the residues were washed with ethyl acetate and the solvent evaporated from the combined filtrates. The crude product was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (9:1) as an eluent to give methoxytolans.

The synthetic route of 171290-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KENT STATE UNIVERSITY; SUMMA HEALTH SYSTEM; WO2008/157745; (2008); A1;,
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Application of 929-75-9, A common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, 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.

General procedure: A two-necked flask equipped with a condenser and magnetic stirrer, flushed with dry argon, wascharged with compounds 14 or 15 (0.2 mmol), Pd(dba)2 (18.4 mg, 16 mol%), RuPhos (16.8 mg,18 mol%), 10 ml absolute dioxane was added followed by corresponding oxadiamine 3a-d (0.4mmol) and sodium tert-butoxide (1.2 mmol, 115 mg). The reaction mixture was stirred at refluxfor 24 h, cooled down to room temperature, the residue was filtered off and washed with 5 mldichloromethane. The combined organic fractions were evaporated in vacuo, the residue wasdissolved in 5 ml dichloromethane, washed by water (3×5 ml), dried over molecular sieves 4A,the solvent was evaporated in vacuo and chromatographed on silica gel using a sequence ofeluents: CH2Cl2, CH2Cl2/MeOH 100:1 – 3:1, CH2Cl2/MeOH/NH3aq 100:20:1 – 100:20:4.

The synthetic route of 929-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chernichenko, Nataliya M.; Averin, Alexei D.; Beletskaya, Irina P.; Letters in Organic Chemistry; vol. 15; 5; (2018); p. 425 – 430;,
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