Ethers-buliding-blocks

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. 24332-20-5, name is 1,1,2-Trimethoxyethane, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H12O3

To a mixture of 2-amino-4-chlorobenzaldehyde (800 mg, 5.13 mmol), 1,1,2-trimethoxyethane (0.78 mL, 6.15 mmol), and p-toluenesulfonic acid monohydrate (194 mg, 1.03 mmol) in toluene (20 mL) was stirred at reflux using a Dean-Stark trap for 3 hr under N2. The mixture was concentrated under reduced pressure and the residue was purified by column chromatography (eluted with PE/EtOAc=4/l) to give 7-chloro-3-methoxyquinoline (300 mg, 30.3% yield). LC-MS: m/z: 194 (M+H)+.

According to the analysis of related databases, 24332-20-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SPERO THERAPEUTICS, INC.; ZAHLER, Robert; (262 pag.)WO2016/112088; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 22236-10-8, name is 4-(Difluoromethoxy)aniline, belongs to ethers-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 22236-10-8, category: ethers-buliding-blocks

General procedure: To a solution of ethyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)benzoate (7) (1 mmol) in ethanol, aryl amines 8 (1 mmol) were added and the resulting mixture was refluxed for 5 – 6 h. The reaction was monitored by TLC. After the completion of the reaction, ethanol was distilled under reduced pressure, and the residue was treated with 10% NaHCO3 solution (20 mL). The aqueous phase was extracted with ethyl acetate (2 x 20 mL) and dried over anhydrous sodium sulphate, which was concentrated to give crude products which were purified by column chromatography over silica gel using chloroform-ethyl acetate (9:1; v:v) as eluent to give pure ethyl 4-(4-(arylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)benzoate 9.

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, 4-(Difluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Roopashree, Rangaswamy; Swaroop, Toreshettahally Ramesh; Jagadish, Swamy; Mohan, Chakrabhavi Dhananjaya; Rangappa, Kanchugarakoppal Subbegowda; Letters in drug design and discovery; vol. 11; 10; (2014); p. 1143 – 1148;,
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Application of 82830-49-7,Some common heterocyclic compound, 82830-49-7, name is 2-Fluoro-1,4-dimethoxybenzene, molecular formula is C8H9FO2, 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.

2-fluoro-3,6-dimethoxybenzaldehydeInto a 500-mL 3-necked round-bottom flask, was placed a solution of 2-fluoro-1,4-dimethoxybenzene (9.4 g, 60.20 mmol, 1.00 equiv) in THF (200 mL). The solution was stirred at -78 C. with stirring, to which was added a solution of n-BuLi/hexane (26.5 mL, 66.3 mmol, 1.10 equiv) dropwise with stirring at -78 C. The resulted solution was stirred for 1 h at -78 C. Then to it was added a solution of N,N-dimethylformamide (8.80 g, 120.40 mmol, 2.00 equiv) in tetrahydrofuran (20 mL) dropwise with stirring at -78 C. After the addition, the reaction solution was allowed to warm up to room temperature and stirred for 2 h. The reaction was quenched by the addition of 100 mL of water. The reaction mixture was extracted with 400 mL of ethyl acetate. The organic layers were combined, washed with 100 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 12.0 g (crude) of 2-fluoro-3,6-dimethoxybenzaldehyde as a yellow solid. LC-MS (ESI) m/z: found for C9H9FO3: 185 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Fluoro-1,4-dimethoxybenzene, its application will become more common.

Reference:
Patent; Global Blood Therapeutics, Inc.; Li, Zhe; Xu, Qing; Yu, Chul; Yee, Calvin; Gwaltney,, II, Stephen L.; Metcalf, Brian W.; Richards, Steven; Lardy, Matthew A.; Setti, Lina; Sham, Hing; US2015/315198; (2015); A1;,
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22236-10-8, name is 4-(Difluoromethoxy)aniline, 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. Quality Control of 4-(Difluoromethoxy)aniline

(S)-5-(3-Trifluoromethyl-phenyl)-furan-2-carboxylic acid [2-cyclohexyl-1-(2-hydroxy-ethylcarbamoyl)-ethyl]-amide 4 (170 mg, 0.38 mmol) was dissolved in CH2Cl2 (5 mL, 0.07M) under a N2 atmosphere. Dess-Martin Periodinane (210 mg, 0.49 mmol, 1.3 eq.) was added in one portion and allowed the reaction to stir at room temperature for 3 hours. After the reaction was judged to be complete by TLC, the reaction was diluted with EtOAc (50 mL) and extracted with 1M sodium thiosulfate (30 mL). The organic layer was extracted with saturated NaHCO3 and saturated NaCl. The organic layer was dried over MgSO4 and filtered. The organic solvent was removed in vacuo and the resulting aldehyde (158 mg, 0.35 mmol, 93%) was used directly without storage: R=0.67 (1:1 hexanes:EtOAc). The aldehyde (43 mg, 0.10 mmol) was dissolved in MeOH (2.5 mL, 0.04M) and brought to 0 C. in an ice bath. 4-Difluoromethoxyaniline (50 muL, 0.31 mol, 3.3 eq.) and acetic acid (20 mL, 0.34 mmol, 3.6 eq.) were added via syringe followed by sodium cyanoborohydride (20 mg, 0.32 mmol) in one portion. The clear reaction mixture was allowed to slowly warm to room temperature and monitored to completion by LC/MS. The reaction was worked up by rotary evaporation of MeOH, dilution with EtOAc (20 mL) and water (20 mL). The organic phase was separated and washed with 1M NaOH (15 mL) and saturated NaCl (15 mL). The organic layer was dried over MgSO4, filtered, and concentrated by rotary evaporation. Purification by mass-directed HPLC, evaporation and lyophilization provided (S)-5-(3-Trifluoromethyl-phenyl)-furan-2-carboxylic acid {2-cyclohexyl-1-[2-(4-difluoromethoxy-phenylamino)-ethylcarbamoyl]-ethyl}-amide 5 as a white amorphous solid (15 mg, 0.02 mmol, 22%): 1H NMR (CD3OD, 400 MHz) delta 0.95-1.06 (m, 2H), 1.19-1.29 (m, 3H), 1.40-1.44 (m, 1H), 1.66-1.86 (m, 7H), 3.26-3.29 (m, 2H), 3.43-3.46 (m, 2H), 4.64 (dd, 1H, J=9.2, 6.0 Hz), 6.59 (t, 1H, J=74.8 Hz), 6.76 (d, 2H, J=8.8 Hz), 6.95 (d, 2H, J=8.8 Hz), 7.11 (s, 1H), 7.29 (d, 1H, J=3.6 Hz), 7.66 (s, 2H), 8.13 (s, 1H), 8.25 (s, 1H); HPLC-MS calcd. for C30H32F5N3O4 (M+H+) 594.2, found 594.5.

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

Reference:
Patent; IRM LLC; US2004/198780; (2004); 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 54149-17-6 as follows. Application In Synthesis of 1-Bromo-2-(2-methoxyethoxy)ethane

Syntheses of Monofunctional Azides:1-Azido-2-(2-methoxyethoxy)ethane, 19. A solution of 1-bromo-2-(2-methoxyethoxy) ethane (12.4 g, 67.8 mmol) and sodium azide (13.2 g, 203 mmol) in water (150 ml) was stirred under reflux for 16 hours. The aqueous phase was extracted with dichloromethane (2¡Á200 ml), dried with MgSO4 and evaporated to dryness, to give 19 as a colorless oil in 87.3% yield. 1H NMR (500 MHz, CDCl3): delta=3.29 (s, CH3O, 3H), 3.30 (t, J=5.2 Hz, CH2N3, 2H), 3.44-3.48 (m, CH3OCH2, 2H), 3.53-3.60 (m, CH2OCH2, 4H). 13C NMR (125 MHz, CDCl3): delta=50.89 (s, CH2N3, 1C), 59.27 (s, CH3O, 1C), 70.29 (s, CH3OCH2CH2, 1C), 70.84 (s, CH3OCH2CH2, 1C), 72.21 (s, CH2CH2N3, 1C).

According to the analysis of related databases, 54149-17-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Scripps Research Institute; US2009/69561; (2009); A1;,
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Related Products of 30568-44-6, 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. 30568-44-6, name is 2-(4-Methoxyphenyl)propan-2-amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: (3S,4S)-4-{[4-(1H-Benzimidazol-2-yl)piperazin-1-yl]carbonyl}-3-(thiophen-3-yl)cyclohexanone (30 mg, 0.07 mmol) was dissolved in a mixture of MeOH (367 muL) and DCE (367 muL), and 2-(4-methoxyphenyl)propan-2-amine (59.2 mg, 0.29 mmol) was added followed by MP-cyanoborohydride (159 mg, 0.367 mmol) and acetic acid (13.0 muL, 0.22 mmol) at rt. The reaction mixture was shaken overnight at 55 C, cooled to rt, filtered and concentrated under vacuum. LC-MS indicated a 3:2 ratio of diastereomeric reductive amination products.

The synthetic route of 2-(4-Methoxyphenyl)propan-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Anthony Romero; Hastings, Nicholas B.; Moningka, Remond; Guo, Zhiqiang; Wang, Ming; Di Salvo, Jerry; Lei, Ying; Trusca, Dorina; Deng, Qiaolin; Tong, Vincent; Terebetski, Jenna L.; Ball, Richard G.; Ujjainwalla, Feroze; Bioorganic and Medicinal Chemistry Letters; vol. 22; 2; (2012); p. 1014 – 1018;,
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Application of 437-83-2, 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 437-83-2 as follows.

Compound 123: 4-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9- tetrahydro-5H-pyrimido[4,5-b][l,4]diazepin-2-ylamino)-2-fluoro-3-methoxybenzoic acid; [0590] 4-Bromo-3-fluoro-2-methoxyaniline: To 3-fluoro-2-methoxyaniline (2.8 g, 20 mmol) in 10 mL of acetic acid was added bromine (0.82 mL, 16 mmol) in acetic acid (10 rnL) dropwise. The reaction mixture was stirred at rt. for 30 min. Solid was filtered and washed with acetic acid to give the HBr salt. It was then dissolved in water, basified by addition of KOH, extracted with ethyl acetate. The organic layer was dried and concentrated to give a white solid (2.8 g, 80 %). 1U NMR (400 MHz, CHLOROFORM-J) delta ppm 3.93 (s, 3 H) 6.42 (dd, J=S.6, 1.8 Hz, 1 H) 7.01 (dd, J=8.6, 7.1 Hz, 1 H). [M+H] calc’d for C7H7BrFNO, 222; found 222.

According to the analysis of related databases, 437-83-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/42711; (2009); 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. 5961-59-1, name is 4-Methoxy-N-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Methoxy-N-methylaniline

4-Acetyl-N-(4-methoxy-phenyI)-N-methyl-benzamide 152. To a stirred solution of 4-acetylbenzoic acid (0.164 g, 1 mmol) and N-methyl-j?-anisidine (0.165 g, 1.2 mmol) in dry DCM (5 mL) and NEt3 (0.17 mL) was added DMAP (catalytic) and the solution was cooled on ice. To this was then added EDCI (0.383 g, 2 mmol) and the reaction was allowed to warm to rt with stirring over 22 h. To this was added sat. aq. bicarb, and DCM and the organic layer was separated and concentrated under reduced pressure. Purification by flash chromatography using an elution gradient of hexane to 30percent EtOAc in hexane gave the title compound, 0.186 g5 66 percent: 1H NMR delta (400 MHz, CDCl3) 2.47 (3H5 s), 3.40 (3H, s), 3.66 (3H5 s), 6.67 (2H5 d, J= 8.6 Hz), 6.89 (2H, d, J= 8.2 Hz)5 7.31 (2H, d5 J= 7.8 Hz)5 7.69 (2H5 d5 J= 7.8 Hz); 13C NMR delta (100 MHz, CDCl3) 26.5, 38.2, 55.2, 114.3, 127.5, 127.9, 128.5, 136.9, 137.0, 140.4, 158.0, 169.5, 197.4; LC/MS (APCI) m/z 304.47 (M-H)-; HPLC tT = 3.61 min (>99percent) 90percent MeCN m H2O.

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 5961-59-1.

Reference:
Patent; STERIX LIMITED; WO2007/96647; (2007); A2;,
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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. 101-84-8, name is Diphenyl oxide, A new synthetic method of this compound is introduced below., Recommanded Product: 101-84-8

(1) diphenyl ether (44.2 g, 0.26 mol) was added into a 250 ml four-necked flask and 123.5 g (1.25 mol) of dichloroethane was added and stirred for 1 hour.Cool to -5 ~ 0 ,Bromine (21 g, 0.13 mol) was rapidly added dropwise and stirred for 1 hour. The mixture was cooled to -5~0 C and 30% hydrogen peroxide (15 g, 0.13 mol)With 0.5 to 1 hour dropwise addition and termination,The temperature is controlled between 0 and 5 DEG C, naturally heated to 25 DEG C after dropping, incubated for 32 hours between 27 DEG C and quenched with 49g of 15% sodium bisulfite, after the phase separation,Then washed with water to neutral, to distill dichloroethane distillation, distillation under reduced pressure before recovery of diphenyl ether, and finally collected 4-bromo-diphenyl ether 51.7g, yield 80.0%, content of 98.2%.

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; Binhai Extensive Chemical Co., Ltd.; Wu Fucai; (8 pag.)CN106957220; (2017); A;,
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These common heterocyclic compound, 16452-01-0, name is 3-Methoxy-4-methylaniline, 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. Recommanded Product: 3-Methoxy-4-methylaniline

To 6.05 g of dichlorophenylborane dissolved in 40 ml of dichloromethane, at -20 C., are successively added 5.226 g of 3-methoxy-4-methylaniline dissolved in 50 ml of dichloromethane, and 13.4 ml of triethylamine dissolved in 25 ml of dichloromethane. After 30 minutes at -20 C., 5.412 g of 2,6-difluorobenzaldehyde dissolved in 60 ml of dichloromethane are introduced. After 24 hours at room temperature, the mixture is hydrolyzed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. To the oil obtained, dissolved in 80 ml of diethyl ether, are added 80 ml of 2 M sodium hydroxide solution and the mixture is left stirring for 18 hours. The phases are separated by settling and the organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is solidified with n-pentane to give 5.069 g of the expected product. 1H NMR delta in ppm (DMSO d6): 1.98 (s, 3H); 3.69 (s, 3H); 4.74 (s, 2H); 5.79 (d, 1H); 5.98 (d, 1H); 6.30 (s, 1H); 6.75 (s, 1H); 7.06 (m, 2H); 7.41 (m, 1H).

The synthetic route of 3-Methoxy-4-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; US2007/185136; (2007); A1;,
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