Month: February 2021

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. 7664-66-6, name is 4-Isopropoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H13NO

Phenyl chloroformate (15.2 kg, 97.1 mol) was dissolved in toluene (115.7 kg) and cooled to 3 0C. 4-isopropoxyaniline (III) (13.3 kg, 88.0 mol) was mixed with acetonitrile (43.4 kg) and slowly added to the phenyl chloroformate solution over 1 hour 40 minutes, followed by slow addition of triethylamine (9.8 kg, 96.8 mol) over 46 minutes. The mixture was heated to 17.5 0C and stirred for 3 hours 30 minutes until the reaction was deemed complete by HPLC. The product solution was washed with IN HCl, followed by removing acetonitrile though an azeotropic distillation with additional toluene (52.3 kg). The solution was heated to 58 0C before slowly adding heptane (43.7 kg) over 1 hour 2 minutes, after which the slurry was cooled to 23.5 0C over 2 hours 35 minutes and stirred for an additional 2 hours 51 minutes. The material was isolated, washed twice with heptane, and dried at < 40 0C for 3 hours 49 minutes. The product was discharged, yielding 19.1kg of the title compound (HIa) (80% yield, 100% purity HPLC AUC). 1H NMR (300 MHz, CD3OD, delta): 7.38 (m, 4H), 7.19 (m, 3H), 6.86 (d, J = 9Hz 2H), 4.52 (sept, J = 6Hz, IH), 1.28 (d, J = 6Hz, 6H). 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 7664-66-6. Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC; ARMITAGE, Ian; BOURLAND, Michael, E.; BOYLE, Craig, J.S.; COOPER, Martin, Ian; FERDOUS, Abu, J.; LANGSTON, Marianne; WO2010/59239; (2010); A2;,
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These common heterocyclic compound, 175278-09-8, name is 4-Bromo-2-(trifluoromethoxy)aniline, 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. Product Details of 175278-09-8

4-Bromo-2-trifluoromethoxy-phenylamine (13 g, 0.05 mol) and But-2-ynedioic acid diethyl ester (10.3 g, 0.12 mol) were dissolved in EtOH (120ml) in a 500 ml round bottom flask and refluxed. The reaction was monitored by LC-MS. 3 h later; 0.3 eq. but-2-ynedioic acid diethyl ester was added. At t = 5h, the reaction mixture was concentrated down to remove the solvent under vacuum, a thick oil was obtained and was used without purification for the next step. MS [M+H]+ = 426.

The synthetic route of 4-Bromo-2-(trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; CAI, Zhenhong, R.; DU, Zhimin; JI, Mingzhe; JIN, Haolun; KIM, Choung, U.; MISH, Michael, R.; PHILLIPS, Barton, W.; PYUN, Hyung-jung; SHENG, Xiaoning, C.; WU, Qiaoyin; ZONTE, Catalin, Sebastian; WO2011/156610; (2011); A2;,
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Reference of 701-56-4, 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. 701-56-4, name is 4-Methoxy-N,N-dimethylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-(N,N-dimethylamino)-3-nitrosoanisole (123). To a stirred solution of N,N-dimethylanisidine 122 (3.09 g, 20.4 mmol) in 5% HCI (30 ml. ), NaNO2 (1.94 g, 28.2 mmol) in 10 mL water was added dropwise upon ice/water bath cooling, and reaction was stirred for 15 min. The mixture was poured in 200 mL of 3N NaOAc (200 mL) and extracted with EtOAc (3 x 150 mL). The combined extract was washed with sat. NaHCO3 (200 mL), brine (200 mL), dried over Na2SO4 and evaporated to give nitroso derivative 123 (3.68 g, 100%) as brown solid.

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

Reference:
Patent; INVITROGEN CORPORATION; WO2008/76524; (2008); A2;,
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Application of 7252-83-7, 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. 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-morpholinobenzothioamide (2.22 g, 10 mmol) in EtOH (50 mL) were added 2-bromo- 1,1 -dimethoxyethane (1.69 g, 10 mmol) and p-toluenesulfonic acid (1.90 g, 10 mmol). The reaction mixture was heated at 95 C overnight, then cooled to rt and filtered. The filter cake was dried to give the title compound as a yellow solid (2.00 g, 8 1%).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1,1-dimethoxyethane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; ZHANG, Jiancun; WANG, Xiaojun; LIN, Runfeng; CAO, Shengtian; WANG, Zhaohe; LI, Jing; WO2014/12360; (2014); A1;,
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Synthetic Route of 13940-96-0, The chemical industry reduces the impact on the environment during synthesis 13940-96-0, name is 4-Phenoxybenzene-1,2-diamine, I believe this compound will play a more active role in future production and life.

In a 1000 ml flask equipped with a stirring blade and a reflux condenser, 750 g of a methyl t-butyl ether solution containing 12% by mass of 3,4-diaminodiphenyl ether and 150.8 g (1.13 mol) of acetic anhydride were charged, The reaction was carried out for 2 hours under heating reflux. From the reaction solution, about 500 g of methyl t-butyl ether was distilled off under reduced pressure to obtain a concentrated solution. The obtained concentrated liquid was poured into 1,000 g of a 20% sodium hydroxide aqueous solution to precipitate an N, N-diacetylated product of 3,4-diaminodiphenyl ether to obtain a solid-liquid mixture.

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-Phenoxybenzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JFE CHEMICAL CORPORATION; MORI, HIROAKI; (9 pag.)JP2016/6020; (2016); A;,
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Related Products of 38336-04-8, 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. 38336-04-8, name is 2-(Benzyloxy)-1-ethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred solution of compounds 21a, b (0.5mmol) in anhydrous DCM (20mL) was added BOP-Cl (0.6mmol), Et3N (1.5mmol) and the amino parts (3, 4, 8a-l, 9a-d, 13a,b, 14a,b, 16a-i, 18, 22a,b and 23) at room temperature. The mixture was stirred overnight at the same temperature, and washed by H3PO4 solution (1%), saturated NaHCO3 solution and brine, dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by Flash column chromatography (DCM/MeOH, 0-10%) to afford the crude target compounds as yellow solids. The solid was further purified by treating with EtOAc and hexane (11mL, 1: 10) to yield the target compounds (24, 25, 26a-l, 27a-g, 28a,b, 29a,b, 30a-i, 31, 32a,b, 33).

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, 2-(Benzyloxy)-1-ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lv, Kai; Li, Linhu; Wang, Bo; Liu, Mingliang; Wang, Bin; Shen, Weiyi; Guo, Huiyuan; Lu, Yu; European Journal of Medicinal Chemistry; vol. 137; (2017); p. 117 – 125;,
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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. 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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