Month: March 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. 13726-14-2, name is 4-Chloro-3-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 13726-14-2

Ethyl 2-chloro-4-(4-chloro-3-methoxyphenylamino)pyrimidine-5-carboxylate (RJ1- 061): A mixture of ethyl 2,4-dichloropyrimidine-5-carboxylate (0.442 g, 2.0 mmol), 4-chloro-3- methoxyaniline (0.331 g, 2.1 mmol), DIPEA (0.42 mL, 2.4 mmol), and iPrOH (2 mL) was added to a 5 mL microwave vial which was then sealed and placed in a hot oil bath with stirring at 85 C overnight for 17 hours. At this point, a brown solid had formed and this was then washed with iPrOH (10 mL), water (10 mL), iPrOH (10 mL), and hexanes (10 mL) to yield RJ1-061 as a brown solid (0.570 g, 83%). m.p. = 119 C (decomposed). XH NMR (400 MHz, DMSO-) delta 10.27 (s, 1H), 8.81 (s, 1H), 7.48 (d, J= 2.3 Hz, 1H), 7.43 (d, J= 8.6 Hz, 1H), 7.28 (dd, J= 8.6, 2.3 Hz, 1H), 4.37 (q, J= 7.1 Hz, 2H), 3.85 (s, 3H), 1.34 (t, J= 7.1 Hz, 3H). LRMS (ESI+) m/z 342.1 (MC135C135+H)+, 344.0 (MC135C137+H)+, 346.0 (MC137C137+H)+; (ESI-) m/z 339.3 (MC135C135-H)-; HRMS (ESI+) m/z calculated for C14H13CI2N3O3 (M+H)+ 342.04067, found 342.04100.

According to the analysis of related databases, 13726-14-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); 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 6775-78-6 as follows. Computed Properties of C6H4ClN3

Example 15 -3 Synthesis of 6-chloro-3-iodo-imidazo[1,2-b]pyridazine 6-chloroimidazo[1,2-b]pyridazine 1*a (28.0 g, 0.182 mol) was dissolved in DMSO (196 ml). Iodine (55.0 g, 0.219 mol) was then added and the reaction mixture was stirred at room temperature for 36 hours. The mixture was poured onto a saturated aqueous sodium bicarbonate solution (250 ml) and extracted with dichloromethane (2 x 250ml). The organic layer was washed with an aqueous solution of sodium meta bisulfite (250 ml) followed by brine (250 ml). It was then dried (Na2SO4) and evaporated under reduced pressure. The residue was recrystallised from ethyl acetate to give 23 g (75 %) of 6-chloro-3-iodo-imidazo[1,2-b]pyridazine 5* as an off white solid. 1H-NMR (400 MHz, DMSO-d6) : delta = 8.27 (1 H, d, J = 9.5 Hz), 8.02 (1 H, s), 7.46 (1 H, d, J = 9.5 Hz). LCMS-ESI (m/z); found 280.0 [M+H]+.

According to the analysis of related databases, 6775-78-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Ullrich, Axel; Falcenberg, Mathias; EP2818471; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 4152-90-3, 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. 4152-90-3, name is (3-Chlorophenyl)methanamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of 4-tert-butylbenzylamine (1a, 0.3 mmol), K2CO3 (3.7 equiv), and MB (1.0 mol%) in dry MeCN (5 mL) in a Pyrex test tube, purged with an O2 balloon, was stirred and irradiated externally with four 22 W fluorescent lamps for 10 h. Products were purified by filtration through a pad of silica gel (3 mm thick) with Et2O, and the filtrate was concentrated.

The synthetic route of (3-Chlorophenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Okada, Akifumi; Yuasa, Hiroki; Fujiya, Akitoshi; Tada, Norihiro; Miura, Tsuyoshi; Itoh, Akichika; Synlett; vol. 26; 12; (2015); p. 1705 – 1709;,
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Related Products of 2106-02-7, These common heterocyclic compound, 2106-02-7, name is 2-Chloro-4-fluoroaniline, 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.

Example 99 i-^-Chloro^-fluorophenylJ^-^-chloro^-fluorophenylJmethyl^S- piperazinedione (E99)Methyl [[(2-chloro-4-fluorophenyl)methyl](2-oxoethyl)amino](oxo)acetate (0.29 g, 1.0 mmol, prepared as described earlier) and 2-chloro-4-fluoraniline (0.29 g, 2.0 mmol) were dissolved in 2% acetic acid/methanol (10ml) at room temperature. The mixture was stirred for 15 minutes before polymer-supported cyanoborohydride (0.98 g, 4.0 mmol) was added. The mixture was stirred at room temperature overnight, then filtered through an SCX cartridge (Varian, 5g) and the filtrate concentrated in vacuo. The residue was then dissolved in 1-butanol (1.5 ml) and heated to 200 0C by microwave irradiation for 1 hour. The mixture was concentrated in vacuo and purified by mass-directed automated HPLC to yield 1-(2-chloro-4-fluorophenyl)-4-[(2-chloro- 4-fluorophenyl)methyl]-2,3-piperazinedione (0.161 g). LC/MS [M+H]+ = 385, retention time = 2.78 min.

The synthetic route of 2106-02-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; CHAMBERS, Laura Jane; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; STEADMAN, Jon Graham Anthony; WALTER, Daryl Simon; WO2010/125103; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 4152-90-3, 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 4152-90-3 as follows.

A solution of tert-butyl (trans)-2-(6-bromopyridin-3-yl)cyclopropylcarbamate (Intermediate E, 350 mg, 1.118 mmol), 3-chlorobenzylamine (237 mg, 1.677 mmol), Sodium tert-butoxide (161 mg, 1.677 mmol) in 1,4-dioxane (7 mL) was degassed for 30 min, tris(dibenzylidene acetone)dipalladium(0) (51 mg, 0.055 mmol), 4,5-Bis(diphenyl phosphino)-9,0-dimethyl xanthene (193 mg, 0.335 mmol) was added and heated for 4 h at 80¡ã C. After completion, the solvent was removed, the residue was poured into ice cold water (10 mL) and extracted with EtOAc (2*20 mL). The combined extracts were washed with water (10 mL), brine (10 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purified by flash chromatography to give tert-butyl (trans)-2-(6-(3-chlorobenzylamino) pyridin-3-yl)cyclopropyl carbamate (100 mg, yield: 24percent) as white solid.

According to the analysis of related databases, 4152-90-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Laria, Julio Castro-Palomino; Fyfe, Matthew Colin Thor; Pedemonte, Marc Murtinell; Munoz, Alberto Ortega; Valls Vidal, Nurla; US2013/289076; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 918538-05-3, 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. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), 1-methyl-1H-imidazol-4-amine hydrochloride (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

The chemical industry reduces the impact on the environment during synthesis 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 1996-29-8,Some common heterocyclic compound, 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, molecular formula is C6H3BrClF, 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.

n-Butyllithium (2.1 M in hexane; 68 ml, 149 mmol) was added dropwise to a stirred solution of diisopropylamine (15 g, 149 mmol) in anhydrous tetrahydrofuran (700 ml) at -78C under a nitrogen atmosphere. Once the addition was complete the reaction mixture was allowed to warm to 00C, cooled to -78C and a solution of 1-bromo-4- chloro-2-fluorobenzene (25 g, 119 mmol) in anhydrous tetrahydrofuran (60 ml) was added dropwise. The mixture was allowed to warm to -200C, cooled to -78C and a solution of trimethylborate (15 g, 143 mmol) in anhydrous tetrahydrofuran (30 ml) added dropwise. The reaction mixture was allowed to warm to -200C and stirred at that temperature for 30 minutes, then cooled to -78C and peracetic acid (80 ml) added dropwise. The mixture was allowed to warm to ambient temperature and stirred overnight under nitrogen. Water (1 I) was added and the resulting mixture extracted with ethyl acetate (3 x 500 ml). The combined organic extracts were washed with water and brine, dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica using 2% ethyl acetate in hexane as eluent to provide 3-bromo-6-chloro-2-fluorophenol (13.8 g, 51%).

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

Reference:
Patent; SYNGENTA LIMITED; WHITTINGHAM, William Guy; WINN, Caroline Louise; GLITHRO, Harry; ASPINALL, Mary Bernadette; SCREPANTI, Claudio; WO2010/125332; (2010); A1;,
Chloride – Wikipedia,
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Reference of 41965-95-1, 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. 41965-95-1 name is 3-Chloro-4-methoxybenzylamine Hydrochloride, 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.

In THF (150 mL) was suspended 3-chloro-4-methoxybenzylamine hydrochloride salt (16.0 g, 76.9 mmol). The suspension was cooled in an ice bath, and triethylamine (19.4 g, 192.3 mmol) was added dropwisely. The reaction mixture was stirred at ambient temperature for 15 min, then was added ethyl 4-chloro-2-thiomethyl-5-pyrimidine carboxylate (14.9 g, 64.1 mmol). The reaction mixture was stirred at ambient temperature overnight. TLC was used to monitor the reaction. After the completion of the reaction, the solvent was removed by rotary evaporation. Acetic ether (500 mL) and water (200 mL) were added. The organic phase was separated, washed with hydrochloric acid (1N), saturated aqueous solution of sodium bicarbonate and brine, dried over sodium sulfate and filtrated. The filtrate was concentrated under reduced pressure. The solvent was removed by rotary evaporation to give oil. Methanol (100 mL) was added to precipitate a large amount of white solid. The mixture was filtrated and the solid was dried in vacuum to give ethyl 4-((3-chloro-4-methoxybenzyl)amine)-2-thiomethyl-5-pyrimidine carboxylate (21 g, 74.2 % yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-4-methoxybenzylamine Hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; WANG, Aichen; EP2886540; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 2106-04-9,Some common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-fluoroaniline, molecular formula is C6H5ClFN, 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: A round-bottomed flask was charged with 2-bromoaniline or 2-fluoro-aniline (>3 g, 1.0 equiv) and potassium O-ethyl carbonodithioate(1.5-1.7 equiv). The mixture was dissolved in DMF (10 volumes) andheated to 120-130 C until the aniline was fully consumed (3-14 h).The reaction mixture was cooled to r.t. and filtered. The filtrate wasdiluted with H 2 O (50 volumes) and the pH was adjusted to 1-2 usingaqueous 2 M HCl. The solid precipitate was collected, washed withH 2 O and dried to yield the pure product.

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wimmer, Laurin; Parmentier, Michael; Riss, Bernard; Kapferer, Tobias; Ye, Chao; Li, Lei; Kim, Hongyong; Li, Jialiang; Synthesis; vol. 50; 10; (2018); p. 2027 – 2032;,
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Related Products of 106131-61-7,Some common heterocyclic compound, 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, molecular formula is C2Cl2N4, 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 solution of 3,6-dichloro-1,2,4,5-tetrazine (500 mg, 3.31 mmol) in Tol. (5 mL) was added 2-methylbut-3-yn-2-ol at 20 C. The mixture was stirred at 115 C. for 16 hours under sealed tube. LCMS showed desired MS. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether:ethyl acetate=10:1 to 4:1, TLC) to give 33a. MS mass calculated for [M+1]+ (C7HCl2N2O) required m/z 207.0, LCMS found m/z 207.0; 1H NMR (400 MHz, CDCl3) delta 7.98 (s, 1H) 2.17 (s, 1H) 1.77 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,6-Dichloro-1,2,4,5-tetrazine, its application will become more common.

Reference:
Patent; Terns, Inc.; KIRSCHBERG, Thorsten A.; HALCOMB, Randall; XU, Yingzi; ROMERO, F. Anthony; US2020/62742; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics