Tag: M.W=100-200

Application of 74654-07-2, The chemical industry reduces the impact on the environment during synthesis 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, I believe this compound will play a more active role in future production and life.

Weigh A4 (0.841 g, 1 mmol) in 15 ml DMF in a 25 ml one-neck flask and add NMM (N-methylmorpholine) (112 muL, 1.0 mmol) and HATU Benzotriazole) -N, N, N ‘, N’-tetramethyluronium hexafluorophosphate) (0.57 g, 1.5 mmol) was activated for 30 min.Add PEG163 (0.163g, 1mmol) with stirring for 1h, then warmed to room temperature for reaction for 10h. The reaction was stopped and dichloromethane was added for extraction. The mixture was washed twice with water and twice with saturated NaCl solution. The organic phase was distilled under reduced pressure to give 0.91g of light yellow solid. Column chromatography white solid 0.651g, 65.08% yield.

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

Reference:
Patent; Shanghai Jiao Tong University; Shen Yumei; Gong Bing; Tan Lianjiang; Shao Zhifeng; Yang Qinglai; Li Xiaowei; Jiang Yu; Zhang Zhen; (42 pag.)CN104693258; (2017); B;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 1159512-64-7, 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 1159512-64-7 as follows.

(a) 4-bromo-2-fluoro-3-(trifluoromethoxy)aniline To a solution of 2-fluoro-3-(trifluoromethoxy)aniline (1.0 g, 5.13 mmol) dissolved in DMF (2 mL) at 0 C. was slowly added a solution of cold N-bromosuccinimide (0.91 g, 5.13 mmol) dissolved in DMF (6 mL) over 5 min. The reaction mixture was stirred at 0 C. for 1 h, extracted with EtOAc (125 mL) and washed with water (3*25 mL). The combined aqueous layers were extracted with EtOAc (75 mL). The combined organic layers were washed with brine (25 mL), dried over sodium sulfate, filtered, and concentrated to produce the title compound as a dark colored liquid (1.27 g, 90% yield). (m/z): [M+H]+ calcd for C7H4BrF4NO 273.94. found 273.8.

According to the analysis of related databases, 1159512-64-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LONG, Daniel D.; MCKINNELL, Robert Murray; JIANG, Lan; LOO, Mandy; LEPACK, Kassandra; VAN ORDEN, Lori Jean; OGAWA, Gavin; HUANG, Xiaojun; ZHANG, Weijiang; US2013/115194; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H13NO

A solution of (3-methoxy-benzyl)-methyl-amine (0.590 g, 3.93 mmol) and TEA (1.1 ml_) in DCM (5 mL) was treated with 2-bromo-1-thiophen-3-yl-ethanone (1.11 g, 5.11 mmol). After 16 h at 23 0C, the mixture was poured onto water and extracted with DCM. The organic layer was collected, dried (Na2SO4), and concentrated to give the desired product (1.149 g, >100% crude). 1H NMR (CDCI3): 8.24 (ddLambda J = 2.9,’ 1.2, 1 H), 7.57 (dd, J = 5.1 , 1.2, 1 H), 7.28 (dd, J = 5.1 , 2.9, 1 H), 7.26-7.21 (m, 1 H), 6.94-6.90 (m, 2H), 6.83-6.79 (m, 1 H), 3.79 (s, 3H), 3.65 (s, 2H), 3.64 (s, 2H), 2.37 (s, 3H).

According to the analysis of related databases, 41789-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2006/66197; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 651734-54-2, name is 2,6-Difluoro-3,5-dimethoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H9F2NO2

To a stirred solution of 2,6-difluoro-3,5-dimethoxyaniline (0.4g, 2.11 mmol) and 6-chloro nicotinaldehyde (0.44g, 3.17 mmol) in toluene (20mL) was added catalytic PTSA and molecular sieves (0.4 g). Heated the reaction mass to reflux in a Dean Stark apparatus for overnight. Concentrated the reaction mass and diluted the residue with methanol, cooled to 0 C and added sodium borohydride (0.3g, 8.4 mmol). Stirred the reaction mass at room temperature for lh and further heated to 70 C for lh. Quenched the reaction mass with ice cold water, warmed to room temperature and diluted with ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate (3x30mL). The organic phase was washed with brine, dried over Na2S04, filtered and concentrated under vacuum. The crude material was purified by silica column chromatography to afford desired title compound (0.2g, 30%) as a solid. LCMS: m/z = 315.1 (M+H)+.

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 651734-54-2.

Reference:
Patent; EISAI R & D MANAGEMENT CO., LTD.; REYNOLDS, Dominic; HAO, Ming-Hong; WANG, John; PRAJAPATI, Sundeep; SATOH, Takashi; SELVARAJ, Anand; (128 pag.)WO2016/164703; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 592-55-2, These common heterocyclic compound, 592-55-2, name is 1-Bromo-2-ethoxyethane, 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. 2-Ethoxyethoxynitrobenzene 2-Nitrophenol (91.0 g., 0.65 mole), 2-bromoethyl ethyl ether (100.0 g., 0.65 mole), anhydrous potassium carbonate (9.0 g, 0.72 mole) and acetone (1 liter) were refluxed for 65 hours. The reaction mixture was filtered, and the acetone removed by rotary evaporation. The residue was partitioned between 200 ml. of dichloromethane and 100 ml water. The organic phase was further washed with 200 ml. of 10% sodium hydroxide followed by 100 cc of water. The product (58.0 g) was obtained in 42% yield by a vacuum distillation (100-120 C./0.5 mm).

Statistics shows that 1-Bromo-2-ethoxyethane is playing an increasingly important role. we look forward to future research findings about 592-55-2.

Reference:
Patent; GAF Corporation; US4203901; (1980); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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: 702-24-9

To a solution of 2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethyl methanesulfonate (1.65 g, 4.44 mmol, Intermediate AO), 1-(4-methoxyphenyl)-N-methyl-methanamine (671 mg, 4.44 mmol) in DMF (20.0 mL) was added K2CO3 (1.23 g, 8.88 mmol). The mixture was stirred at 20 C. for 15 hours. On completion, the mixture was diluted with H2O (60 mL), then extracted with EA (3¡Á30 mL). The organic layers were washed with brine (3¡Á30 mL) and dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The mixture was purified by reverse phase: (0.1% FA) to give the title compound (700 mg, 36% yield) as yellow oil. 1H NMR (400 MHz, CDCl3) delta 8.52 (s, 1H), 7.33 (d, J=8.4 Hz, 2H), 6.90 (d, J=8.8 Hz, 2H), 3.87 (s, 2H), 3.83 (s, 3H), 3.81-3.75 (m, 2H), 3.68-3.61 (m, 8H), 3.56-3.48 (m, 2H), 3.38-3.25 (m, 2H), 2.96-2.84 (m, 2H), 2.48 (s, 3H), 1.46 (s, 9H).

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

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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

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,
Ether | (C2H5)2O – PubChem

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

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,
Ether | (C2H5)2O – PubChem