Month: March 2021

Reference of 349-65-5, 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. 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

B2a. General Method for Reaction of an Aryl Amine with Phosgene Followed by Addition of a Second Aryl Amine; [] N-(2-Methoxy-5-(trifluoromethyl)phenyl)-N’-(3-(4-pyridinylthio)phenyl)urea: To a solution of pyridine (0.61 mL, 7.5 mmol, 3.0 equiv) and phosgene (20% in toluene; 2.65 mL, 5.0 mmol, 2.0 equiv) in CH2Cl2 (20 mL) was added 2-methoxy-5-(trifluoromethyl)aniline (0.48 g, 2.5 mmol) at 0 C. The resulting mixture was allowed warm to room temp. stirred for 3 h, then treated with anh. toluene (100 mL) and concentrated under reduced pressure. The residue was suspended in a mixture of CH2Cl2 (10 mL) and anh. pyridine (10 mL) and treated with 3-(4-pyridinylthio)aniline (0.61 g, 2.5 mmol, 1.0 equiv). The mixture was stirred overnight at room temp., then poured into water (50 mL) and extracted with CH2Cl2 (3 x 25 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The residue was dissolved in a minimal amount of CH2Cl2 and treated with pet. ether to give the desired product as a white precipitate (0.74 g, 70%): mp 202 C; TLC (5% acetone/95% CH2Cl2) Rf 0.09; 1H-NMR (DMSO-d6) delta 7.06 (d, J=5.5 Hz, 2H), 7.18 (dd, J=2.4, 4.6 Hz, 2H), 7.31 (dd, J= 2.2, 9.2 Hz, 1H), 7.44 (d, J=5.7 Hz, 1H), 7.45 (s, 1H), 7.79 (d, J=2.2 Hz, 1H), 8.37 (s, 2H), 8.50 (dd, J=2.2, 9.2 Hz, 2H), 9.63 (s, 1H), 9.84 (s, 1H); FAB-MS m/z 420 ((M+H)+, 70%).

The synthetic route of 2-Methoxy-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharmaceuticals Corp.; EP1042305; (2005); B1;,
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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. 80936-82-9, name is 4-(Methoxymethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 80936-82-9

The reaction of 2,4-dichloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazine and 4-methoxymethylphenylamine using the method described in Example 37 provided the title compound (45 mg, 13% yield). 1H NMR (DMSO-d6) 9.60 (br s, 1H), 7.77 (m, 1H), 7.44 (s, 2H), 7.40-7.43 (m, 2H), 7.32 (m, 1 H), 7.21-7.23 (m, 4H), 4.34 (s, 2H), 3.26 (s, 3H), 2.52 (s, 3H).

According to the analysis of related databases, 80936-82-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cell Therapeutics, Inc.; US2003/153570; (2003); A1;,
Ether – Wikipedia,
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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. 2674-34-2, name is 1,4-Dibromo-2,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., Product Details of 2674-34-2

A flame dried RBF was charged with l,4-dibromo-2,5-dimethoxybenzene (1) (10.3 g, 39.6 mmol, 1.0 equiv.), phenylboronic acid (9.92 g, 81.4 mmol, 2.05 equiv.), potassium carbonate (19.2 g, 139 mmol, 3.5 equiv.), toluene (80 mL), deionized water (40 mL), and a stir bar. Pd(PPh3)4 (457 mg, 0.395 mmol, 1 mol%) was added last to the flask before the reaction mixture was lowered into a bath that was preheated to 90 C and stirred for l2h with a condenser. Upon completion, the reaction was diluted with water, extracted 3 times with DCM, dried on MgS04, and concentrated via rotary evaporation. The solid was then recrystallized in EtOH to provide 9.01 g (31.1 mmol, 78% yield) of white needles. NMR (500 MHz, CDCb): d 7.61-7.59 (m, 4H), 7.46-7.43 (m, 4H), 7.38-7.34 (m, 2H), 6.99 (s, 2H), 3.80 (s, 6H). 13C NMR (125 MHz, CDCb): d 150.6, 138.3, 130.4, 129.4, 128.1, 127.1, 114.8, 56.4. HRMS (TOF-EI, m/z) calcd. for C20H18O2 [M]+: 290.1307; found: 290.1300.

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; LEHIGH UNIVERSITY; CHEN, Mark; WEHRMANN, Caleb; CHARLTON, Ryan; (58 pag.)WO2019/226678; (2019); A2;,
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Related Products of 701-07-5, 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 701-07-5 as follows.

To a suspended solution of Mg chips (10.07 g, 0.414 mol) in anhydrous ether (150 mL) at 22C under argon was added ca. 0.15 mL of 1,2-dibromoethane. Then 43.7 g (0.200 mol) of 2-(isopropoxy)bromobenzene in 200 mL of ether was added dropwise. After 50% of the aryl halide was added, the reaction began to reflux vigorously. The flask was cooled in an ice bath. After the refluxing had subsided somewhat, the ice bath was removed and the remaining aryl halide was added over a 1.5 h period. The resultant Grignard reagent was cooled in a dry ice/ether bath for 2 h and then treated with 34.0 mL (0.221 mol) of 98% 1-carbethoxy-4-piperidone. Upon complete addition of ketone, the reaction mixture was allowed to warm to 22C and stirred for 2 h. The reaction was then quenched with cold aqueous ammonium chloride which resulted in an emulsion. Addition of 1M aqueous HCI solution separated the two layers. The aqueous phase was extracted with additional ether and the combined organic solution was washed with 10% aqueous sodium bisulfite, 1.0 M HCI, saturated NaHCO3, and dried (K2CO3). Filtration and concentration yielded 56.36 g of 1-carbethoxy-4-[2-(1-methylethoxy)phenyl]-4-piperidinol as a yellow viscous oil which was carried on without further purification The structure of this oil was supported by 1H NMR.

According to the analysis of related databases, 701-07-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ORTHO PHARMACEUTICAL CORPORATION; EP736009; (2002); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 36865-41-5 as follows. SDS of cas: 36865-41-5

6-(tert- Butylsulfonyl)-4-chloroquinolin-7-ol (60 mg, 0.196 mmol), K2C03 (55 mg, 0.392 mmol) and l-bromo-3-methoxypropane (0.088 ml, 0.785 mmol) in DMF (1 ml) were heated to 70 C. The reaction mixture was partitioned between EtOAc and brine. The aqueous layer was extracted with EtOAc twice and the combined EtOAc layers were dried over Na2S04, filtered, and concentrated. The residue was purified via Biotage (SNAP Cartridge KP Sil lOg, 30-75% EtOAc/Hexane) to yield 6-(tert-butylsulfonyl)-4-chloro-7-(3- methoxypropoxy)quinoline (0.071 g, 0.185 mmol, 94 % yield). 1H NMR (400 MHz, DMSO-de) delta ppm 1.33 (s, 9 H) 1.99 – 2.08 (m, 2 H) 3.27 (s, 3 H) 3.58 (t, J=6.19 Hz, 2 H) 4.32 (t, J=6.19 Hz, 2 H) 7.73 (s, 1 H) 7.76 (d, J=4.80 Hz, 1 H) 8.65 (s, 1 H) 8.94 (d, J=4.55 Hz, 1 H), MS: m/z: 372.1 [M+H]+.

According to the analysis of related databases, 36865-41-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; CASILLAS, Linda, N.; DEMARTINO, Michael, P.; HAILE, Pamela, A.; MEHLMANN, John, F.; RAMANJULU, Joshi, M.; SINGHAUS, Robert, Jr.; WO2014/43437; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 886762-08-9 as follows. HPLC of Formula: C7H5BrF3NO

Under nitrogen atmosphere, 2.2 mL of anhydrous triethylamine was added dropwise to a solution of 2 g (15.4 mmol) of 1,1-cyclopropanedicarboxylic acid in dichloromethane, and the mixture was stirred for 30 min in an ice bath and then 1.2 mL SOCl2 in dichloromethane,After the addition was complete, the mixture was stirred for 2h, and then 3.5g (13.9mmol) of 5-bromo-2-trifluoromethoxyaniline in dichloromethane was added dropwise to the reaction mixture. After the addition was completed, stirring was continued for 2h. The reaction solution was then adjusted to pH 10 with 2 mol / L NaOH solution, evaporated to dryness under reduced pressure, sonicated with appropriate amount of water, extracted once with ethyl acetate, the aqueous layer was retained,The aqueous layer was further adjusted to pH 2 with 2 mol / L HCl and extracted three times with ethyl acetate.The organic solvent was removed under reduced pressure to give 1 – ({[5-bromo-2- (trifluoromethoxy) phenyl] amino} carbonyl) cyclopropanecarboxylic acid, About 0.8g, yield 35%;

According to the analysis of related databases, 886762-08-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Xi’an Jiaotong University; Zhang Jie; Lu Wen; Su Ping; Wang Jinfeng; Pan Xiaoyan; He Langchong; Wang Sicen; He Huaizhen; (14 pag.)CN105924403; (2016); A;,
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Electric Literature of 36865-41-5, 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 36865-41-5 as follows.

Step 1: Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 1-bromo-3-methoxypropane (60 g, 393.0 mmol), triphenylphosphine (102.8 g, 393.1 mmol) and toluene (300 mL). The resulting solution was stirred for 16 h at 150 C. in an oil bath. The solids were collected by filtration. This resulted in (3-methoxypropyl)triphenylphosphonium bromide (120 g, 91% yield) as a white solid.

According to the analysis of related databases, 36865-41-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Enanta Pharmaceuticals, Inc.; Panarese, Joseph; Bartlett, Samuel; Chong, Katherine; Or, Yat Sun; (120 pag.)US2019/224188; (2019); A1;,
Ether – Wikipedia,
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Electric Literature of 768-70-7, 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. 768-70-7 name is 3-Ethynylanisole, 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.

EXAMPLE 13 : 5-(3-Methoxyphenethyl)-l-(4-chloro-3-fluorobenzyl)pyridin- 2( 1 H)-OiIC (Final Compound 7-06); Step 1 : 5-(3-Methoxyphenethynyl)-2-methoxypyridine According to Scheme 8 Step 1 : Et3N (15eq, 12.0mmol, 1.68mL), PdCl2(PPh3)2 (0.05eq, 0.04mmol, 17.5mg), PPh3 (0.2eq, O.l?mmol, 41.8mg) and 5-bromo-2- methoxypyridine (leq, 0.80mmol, 0.15g) were added to a stirred solution of copper iodide (0.05eq, 0.04mmol, 7.6mg) in DMF (8mL). Then l-ethynyl-3-methoxybenzene (l.leq, 0.88mmol, 0.12g) was added and the mixture was heated under microwaves (120C/25min) and was stirred overnight at room temperature. The resulting solution was poured onto water and extracted with AcOEt. The combined organic layers were dried over MgSO4, filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25g SiO2) using pentane/Et2O 98/2 as eluent to afford 5-(3- methoxyphenethynyl)-2-methoxypyridine (0.64mmol, 154mg, 81%) as a colorless oil. LC (XTerra RP18, 3.5mum, 3.0x50mm Column): RT = 5.13 min; MS m/z ES+= 240.

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

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; ADDEX PHARMACEUTICALS S.A.; WO2006/30032; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 651734-54-2, name is 2,6-Difluoro-3,5-dimethoxyaniline, molecular formula is C8H9F2NO2, 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. SDS of cas: 651734-54-2

Example 451-Cyclopropyl-3-(2,6-difluoro-3,5-dimethoxyphenyl)-1,3,4,7-tetrahydro-2H- pyrrolo j3?,2?:5,6j pyrido 14,3-djpyrimidin-2-one Step 1: N-[(JE)-(4-chloro-JH-pyrrolo[2, 3-bJpyridin-5-yl)methyleneJ-2, 6-d ifluoro-3 , 5- dimethoxyaniline A mixture of 4-chloro- 1 H-pyrrolo[2,3 -b]pyridine-5 -carbaldehyde (5.00 g, 27.7 mmol), 2,6-difluoro-3,5-dimethoxyaniline (6.3 g, 33 mmol) and p-toluenesulfonic acid monohydrate (1.1 g, 5.8 mmol) in toluene (300 mL) was heated to reflux with azeotropic removal of water via a Dean-Stark trap. After stirred for overnight, the reaction mixture wasconcentrated and the residue was used in the next step 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 651734-54-2, its application will become more common.

Reference:
Patent; INCYTE CORPORATION; WU, Liangxing; ZHANG, Colin; HE, Chunhong; SUN, Yaping; LU, Liang; QIAN, Ding-Quan; XU, Meizhong; ZHUO, Jincong; YAO, Wenqing; WO2014/7951; (2014); A2;,
Ether – Wikipedia,
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These common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, 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: 93919-56-3

A solution of the ethyl 3-(3,5-dibromo-4-hydroxyphenyl)-1,2,4-oxadiazole-5-carboxylate (78 mg, 0.2 mmol) plus 4-trifluoromethoxybenzyl amine (57 mg, 0.3 mmol) in ethanol (3 mL) was refluxed for 6 hours. The resulting solution was evaporated in vacuo and the residue was dissolved in ethyl acetate (2.5 mL) and washed with 1 N hydrochloric acid (2 mL), then water (2 mL). The organic layer was evaporated to dryness in vacuo and purified by preparative HPLC to give the title compound (57 mg, 53%) as a colourless powder. 1H NMR delta (ppm) (DMSO-d6): 4.55 (2H, d), 7.38 (2H, d), 7.51 (2H, d), 10.07 (1H, t), 10.95 (1H, s, br). LCMS (10 cm_apci_formic) tR4.14 min; m/z 534/536/538 [M-H]-.

The synthetic route of (4-(Trifluoromethoxy)phenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Institute for OneWorld Health; US2009/318429; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem