Category: 1535-73-5

Adding a certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, 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 1535-73-5, Product Details of 1535-73-5

General procedure: A mixture of B (1 mmol) and dichloromethane (10 ml) was stirred for 10 min, then EDCI (1.2 mmol) and HOBt (1.2 mmol) were added. Added the appropriate amine (1.2 mmol) into the mixed solution after 30 min and refluxed for 12 h. The reaction mixture was filtrated with water and then the filtrate was dried and evaporated. Purification by silica gel afforded C1-C27

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Trifluoromethoxyaniline, and friends who are interested can also refer to it.

Reference:
Article; Ni, Hai-Jun; Cheng, Hui-Jie; Ge, Wei-Wei; Lin, Meng-Xue; Li, Qing-Shan; Ruan, Ban-Feng; Letters in drug design and discovery; vol. 13; 6; (2016); p. 495 – 504;,
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Reference of 1535-73-5,Some common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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.

Example 62: 3-(5-Oxo-4,5,6,7,8,9-hexahydro-2H-1,2,7,9-tetraazabenz[f]inden-4-yl)-N-(4-trifluoromethoxy-phenyl)-benzamide; compound with trifluoro-acetic acid Preparation of the aldehyde: to a solution of 300 mg of 4-carboxybenzaldehyde (2 mmoles) and 382 mg of 4-(trifluoromethoxy)aniline (2 mmoles) in 5 ml of ethyl acetate is added 830 mg of dicyclohexycarbodiimide) (DCC) (4 mmoles). The reaction mixture is heated at 60¡ãC overnight and then poured into 60 ml of 1 N HCl solution. The mixture is extracted with twice 30 ml of ethyl acetate. The combined organic phases are washed with 50 ml of water; 50 ml saturated solution of sodium bicarbonate and brine, dried over MgSO4 and evaporated. The crude is purified on silica gel giving 233 mg of 4-Formyl-N-(3-trifluoromethoxy-phenyl)-benzamide (yield=38percent). ([M+H]+): 310). Ret. Time: 5.60 min (gradient 5 to 85 percent acetonitrile in 7 min).

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

Reference:
Patent; Aventis Pharma S.A.; EP1746097; (2007); A1;,
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Synthetic Route of 1535-73-5,Some common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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.

(Formula 1-2: methyl 4-(((3-(trifluoromethoxy)phenyl)amino)methyl)benzoate)[1723][1724]Compound ofFormula 1-1(3-(trifluoromethoxy)aniline; 0.385 mL, 4.625 mmol), methyl 4-(bromomethyl)benzoate (1.271 g, 5.550 mmol) and DIPEA (1.228 mL, 6.937 mmol) were dissolved in acetonitrile (5 mL) at room temperature and stirred at the same temperature for 16 hours. Water was poured into the reaction mixture, and the organic layer was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution, dehydrated with anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The concentrate was purified and concentrated by column chromatography (silica; ethyl acetate/hexane=20percent) to give the desired compound ofFormula 1-2(0.607 g, 40.3percent) in the form of a white solid.

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

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Changsik; YANG, Hyun-Mo; CHOI, Hojin; KIM, Dohoon; KIM, Soyoung; HA, Nina; LIM, Hyojin; KO, Eunhee; YOON, Seongae; BAE, Daekwon; WO2014/178606; (2014); 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. 1535-73-5, name is 3-Trifluoromethoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H6F3NO

The title compound was prepared according to procedures similar to those described in Example 1 starting from 2-bromo-5-trifluoromethoxy-aniline, which was obtained as follows:A solution of 3-trifluoromethoxy-aniline (1.77 g) in toluene (20 ml) was treated with Lambda/-bromosuccinimide (1.87 g) at ambient temperature and the reaction mixture was stirred for 2 hours at ambient temperature, quenched by addition of water and the mixture extracted with ethyl acetate (3x 50 ml). The combined organic extracts were washed with aqueous sodium hydrogen carbonate (saturated), dried over sodium sulfate and then concentrated in vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane / ethyl acetate 95:5) to afford 4-bromo-3-trifluoromethoxy-aniline (270 mg) and 2-bromo-5- trifluoromethoxy-aniline (1.45 g), which were both characterized by mass and NMR spectra. 4-bromo-3-trifluoromethoxy-aniline: MS (ES+) 256 / 258 (MH+); IH NMR (400 MHz, CDCl3) 3.5 (brs, 2H), 6.5 (d, IH), 6.7 (s, IH), 7.3 (d, IH). 2-bromo-5-trifluoromethoxy- aniline: MS (ES+) 256 / 258 (MH+); IH NMR (400 MHz, CDCl3) 4.2 (brs, 2H), 6.5 (d, IH), 6.6 (s, IH), 7.4 (d, IH).

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 1535-73-5.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; CASSAYRE, Jerome Yves; PITTERNA, Thomas; CORSI, Camilla; MAIENFISCH, Peter; WO2011/3684; (2011); A1;,
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Synthetic Route of 1535-73-5, These common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, 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: An aqueous solution of cesium carbonate (130 mg, 0.4 mmol) in water (300 ul) was dispensed into each well containing a pre-mixed solution of 4-chloro-N-(4-methoxyphenyl)pyridin-2-amine (58.8 mg, 0.2mmol), respective aniline (0.26 mmol), xantphos (13.9 mg, 0.024mmol) and palladium (II) acetate (3.6 mg, 0.016 mmol) in DMA (1.25 ml). The resultant plate was placed on a pre-heated SOPHAS base plate set at 150 oC and shaken for 1 hour. The plate was cooled to room temperature and MP-TMT resin (90 mg) added to each well prior to shaking overnight at room temperature. The following day each well was transferred to a 48 well filter plate, washing through with an extra aliquot of DMA (200 ul) before a final centrifuge. The crude filtrates were then purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5mu silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford required N2-(4-methoxyphenyl)-N4-[aryl]pyridine-2,4-diamine (23-42%)

Statistics shows that 3-Trifluoromethoxyaniline is playing an increasingly important role. we look forward to future research findings about 1535-73-5.

Reference:
Article; Burton, Rebecca J.; Crowther, Mandy L.; Fazakerley, Neal M.; Fillery, Shaun M.; Hayter, Barry M.; Kettle, Jason G.; McMillan, Caroline A.; Perkins, Paula; Robins, Peter; Smith, Peter M.; Williams, Emma J.; Wrigley, Gail L.; Tetrahedron Letters; vol. 54; 50; (2013); p. 6900 – 6904;,
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Reference of 1535-73-5, A common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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 mixture of compound 3B-1 (2.00 g, 8.98 mmol, 1.0 eq) and compound 3D-1 (1.91 g, 10.8 mmol, 1.2 eq) in isopropanol (20 mL) was added TFA (1.02 g, 8.98 mmol, 1.0 eq) in one portion at 20 ¡ãC under nitrogen. The mixture was stirred at 90 ¡ãC for 18 hours. LC-MS (ET15060-21-P1A1) showed the reaction was completed. The resulting suspension was cooled, and the product was filtered off, washing with a small volume of dichloromethane (10 mL) to give compound 3D-2 (3.00 g, 8.26 mmol, 91.9 percent yield) as yellow solid which was used for next step directly. ln NMR: ET15060-21-P1A1 400 MHz DMSO-d6 9.68 (s, 1H), 8.71 (d, J = 8.8 Hz, 1H), 8.15 (d, J = 6.0 Hz, 1H), 8.03 (s, 1H), 7.91 (dd, J = 8.4, 1.2 Hz, 1H), 7.71 (d, J = 8.4, Hz, 1H), 7.45 (t, J = 8.4 Hz, 1H), 6.98 (d, J = 8.0 Hz, 1H), 6.90 (d, J = 6.0 Hz, 1H), 2.48 (s, 3H).

The synthetic route of 1535-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LUTRIS PHARMA LTD.; SHELACH, Noa; (76 pag.)WO2019/26065; (2019); A2;,
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Application of 1535-73-5,Some common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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.

3-(trifluoromethoxy)aniline (50.0 mg, 0.28 mmol), intermediate E (80.0 mg, 0.24 mmol), DMAP (1.5 mg, 0.01 mmol) and DIEA (62.0 mg, 0.48 mmol) in DMF (5 mL) was heated at 85¡ãC for 10h under N2. Water (10 mL) was added and the mixture was extracted with ethyl acetate (2 x 10 mL). The combined organics were dried over Na2SO4 , filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: DCM:MeOH = 15:1) to afford the titled compound (40.0 mg, 30percent) as a yellow solid. (0622) LCMS (method B): 2.66 min [MH]+=566.0. 1H NMR (400 MHz, DMSO-d6) delta 9.53 (s, 2H), 9.44-9.41 (m, 2H), 8.10 – 8.09 (m, 1 H),7.80 – 7.78 (m, 2H), 7.64 (dd, J = 8.4, 2.0 Hz, 1 H), 7.32 (br s, 1 H), 7.20 (br s, 1 H), 7.12-7.07 (m, 2H), 6.96 (d, J = 8.4 Hz, 2H), 6.65 (d, J = 8.4 Hz, 2H), 5.70 (d, J= 6.0 Hz, 1 H), 3.43 (s, 3H, covered), 2.74 (d, J = 3.9 Hz, 3H), 2.25 (s, 3H).

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

Reference:
Patent; CATALYST THERAPEUTICS PTY LTD; LESSENE, Guillaume Laurent; GARNIER, Jean-Marc; CUZZUPE, Anthony Nicholas; FEUTRILL, John Thomas; CZABOTAR, Peter Edward; SHARMA, Pooja; (142 pag.)WO2016/127213; (2016); A1;,
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Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, 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 1535-73-5, COA of Formula: C7H6F3NO

Pentafluorophenyl chlorothionoformate (2.89 mL, 18.01 mmol) in DCM (10 mL) was added dropwise to 3-(Trifluoromethoxy)aniline (2.189 mL, 16.37 mmol) and Pyridine (1.986 mL, 24.56 mmol) in dichloromethane (180 mL) at O0C. The resulting solution was stirred at ambient temperature for 20 hours. The reaction mixture was washed sequentially with IM citric acid (100 mL), saturated NaHCCbeta (100 mL), and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 5 to 15percent ethyl acetate in isohexane. Pure fractions were evaporated to dryness to afford O- perfiuorophenyl 3-(trifluoromethoxy)phenylcarbamothioate (3.70 g, 56.0percent) as a yellow oil. IH NMR (400 MHz, CDC13) delta 7.08 (IH, s), 7.13 – 7.19 (2H, m), 7.38 (IH, t).

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/24821; (2009); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 1535-73-5, 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. 1535-73-5 name is 3-Trifluoromethoxyaniline, 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.

General procedure: The carboxylic acid (0.8 mmol), HATU (hexafluorophosphateazabenzotriazole tetramethyl uranium) (455 mg, 1.2 mmol) and triethylamine (324 mg, 3.2 mmol) were stirred for 30 min in 20 mL dichloromethane. The corresponding amine (1.19 mmol) was added to the reaction mixture and stirred overnight. The resulting solid was filtered, washed with dichloromethane and crystallized from methanol unless otherwise noted. Purification was carried out over silica gel chromatography till purity reached >95percent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Trifluoromethoxyaniline, and friends who are interested can also refer to it.

Reference:
Article; Shahin, Mai I.; Roy, Joyeeta; Hanafi, Maha; Wang, Dongyao; Luesakul, Urarika; Chai, Yifeng; Muangsin, Nongnuj; Lasheen, Deena S.; Abou El Ella, Dalal A.; Abouzid, Khaled A.; Neamati, Nouri; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 516 – 530;,
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Reference of 1535-73-5, The chemical industry reduces the impact on the environment during synthesis 1535-73-5, name is 3-Trifluoromethoxyaniline, I believe this compound will play a more active role in future production and life.

Add 3-(trifluoromethoxy)aniline (1.0 g, 5.65 mmol), pyridine (0.89 g, 11.3 mmol) to DCM (20 mL) and cool to 0 C. Add dropwise phenyl chloroformate (1.15 g, 7.34 mmol). After addition, stir for 1 hr. TLC (PE:EtOAc=3:1) shows the reaction is complete. Add water to the mixture, extract with DCM (10 mL*3), combine the organic layer, wash with 1N HCl solution, brine sequentially, and dry over anhydrous Na2SO4. Concentrate under reduced pressure to get the product (1.50 g, 89%). Intermediates D42-D46 can be synthesized with similar method (Table D9)

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, 3-Trifluoromethoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhang, Deyi; Zhang, Ruihao; Zhong, Boyu; Shih, Chuan; US2015/197511; (2015); A1;,
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