Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 1000577-58-1, name is 1-Bromo-2,3-dichloro-5-fluorobenzene, belongs to chlorides-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 1000577-58-1, Recommanded Product: 1000577-58-1

A mixture of l-bromo-2,3-dichloro-5-fluorobenzene (3.1304 g, 12.94 mmol), bis(pinacolato)diboron (5.7397 g, 22.38 mmol), potassium acetate (3.9788 g, 40.1 mmol) in DMSO (60 mL) was stirred at room temperature for about 30 min. The mixture was degassed with nitrogen for a few minutes and l ,l’-[bis(diphenylphosphino)ferrocene]dichloro- palladium (II) (0.7953 g, 1.09 mmol) was added. The mixture was degassed again with nitrogen, was heated to 80 oc with stirring and kept at 80 oC for 4 h 20 min. The mixture was cooled to room temperature and poured into ice. The mixture was extracted with ethyl acetate (3 x 150 mL). The combined organic solution was washed with saturated sodium chloride solution (150 mL), dried over anhydrous sodium sulfate, and concentrated. The residue was separated with flash column chromatography on silica gel using ethyl acetate/hexane to afford product as white solid (2.6156 g, Yield: 70%). NMR (500 MHz, Chloroform-d) delta 7.070 (d, J= 3.0 Hz, lH), 7.029 (d, J= 3.0 Hz, 1H), 1.238 (s, 12H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2,3-dichloro-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; NEKTAR THERAPEUTICS (INDIA) PVT. LTD.; NEKTAR THERAPEUTICS; SHARMA, PANKAJ; KHATRI, VIJAY KUMAR; GU, XUYUAN; SONG, YUAN; SHEN, MICHAEL LIXIN; SAUTHIER, JENNIFER RIGGS; ANAND, NEEL K.; KOZLOWSKI, ANTONI; ODINECS, ALEKSANDRS; RILEY, TIMOTHY A.; REN, ZHONGXU; MU. YONGQI; SHEN, XIAOMING; YUAN. XUEJUN; AURRECOECHEA, NATALIA; O’MAHONY, DONOGH JOHN ROGER; WO2015/92819; (2015); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 348-65-2, name is 5-Chloro-2,4-difluoroaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Chloro-2,4-difluoroaniline

j00283j A solution of 5-chloro-2,4-difluoro-aniline (5.0 g, 31 mmol) and potassium 0-ethyl carbonodithioate (12 g, 73 mmol) in 1V N-dimethylformamide (50 mL) was stirred at 130 C for 16hours. On completion, the reaction was cooled to room temperature, and iN hydrochloric acid (100 mL) was added. The mixture was stirred for 1 hour, resulting in formation of a solid. The solid was collected by filtration, washed with water (2×100 mL) and dried under vacuum to give compound B- 5(5.6 g, 79% yield) as a white solid. LCMS (B): tR=0.759 mi, (ES)m/z(M+H)=220.1.

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; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 29027-17-6, These common heterocyclic compound, 29027-17-6, name is 2-Chloro-3-methylaniline, 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.

2-Chloro-1-isothiocyanato-3-methylbenzene To 2-chloro-3-methylaniline (1 equiv.) in DCM/water (0.5 M, 1/2) at 0 C. was added NaOH (3 equiv.), the solution was stirred at 0 C. for 5 min, then CSCl2 (3 equiv.) was added. The reaction was stirred at room temperature overnight. The reaction was extracted with DCM. The combined organic layers were concentrated to dryness to give crude 2-chloro-1-isothiocyanato-3-methylbenzene. The crude product was purified by column chromatography on silica gel with petroleum ether to give 2-chloro-1-isothiocyanato-3-methylbenzene (61%) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta ppm: 7.19-7.09 (m, 3H), 2.42 (s, 3H).

Statistics shows that 2-Chloro-3-methylaniline is playing an increasingly important role. we look forward to future research findings about 29027-17-6.

Reference:
Patent; Signal Pharmaceuticals, LLC; Alexander, Matthew; Bahmanyar, Sogole; Hansen, Joshua; Huang, Dehua; Hubbard, Robert; Jeffy, Brandon; Leisten, Jim; Moghaddam, Mehran; Raheja, Raj K.; Raymon, Heather; Schwarz, Kimberly; Sloss, Marianne; Torres, Eduardo; Tran, Tam Minh; Xu, Shuichan; Zhao, JingJing; Boylan, John Frederick; (317 pag.)US2016/96841; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 69411-05-8 as follows. Quality Control of 3-Chloro-5-trifluoromethylaniline

Intermediate E (120 mg, 0.25 mmol), 3-chloro-5-(trifluoromethyl)benzenamine (49 mg, 0.27 mmol) and DMAP (16 mg, 0.125 mmol) were dissolved in THF (15 mL). The reaction mixture was heated to 85 C for 16 hours. The solvent was removed and the crude product was purified by column chromatography (DCM: methanol 100/0 to 98/2) to give 5-((4-((4-(3-(3-chloro-5- (trifluoromethyl)phenyl)ureido)phenyl)(methyl)amino)pyrimidin-2-yl) amino)-N,2- dimethylbenzamide (38 mg, 26%) as a white solid. LCMS (method B): 2.74 min [MH]+=584.1. 1H NMR (400 MHz, DMSO-d6) delta ppm 2.23 (s, 3 H) 2.74 (d, J=4.8 Hz, 3 H) 3.41 (s, 3 H) 5.77 (d, J= 7.0 Hz, 1 H) 7.07 (d, J= 8.4 Hz, 1 H) 7.28 (d, J= 8.8 Hz, 2 H) 7.43 (s, 1 H) 7.59 (d, J= 8.8 Hz, 2 H) 7.67 (dd, J=8.4 2.0 Hz, 1 H) 7.87 (m, 4 H) 8.11 (m, 1 H) 9.15 (s, 1 H) 9.19 (s, 1 H) 9.37( s, 1 H).

According to the analysis of related databases, 69411-05-8, the application of this compound in the production field has become more and more popular.

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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 179897-90-6, A common heterocyclic compound, 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, molecular formula is C6H2Br2ClF, 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 150 mL of DMF (dimethylformaldehyde), 1,3-dibromo-2-chloro-5-fluorobenzene (23.0 g, 79.8 mmol), dimethylamine (24.3 g, 144 mmol) and cesium carbonate (84.4 g, 239 mmol) were added thereto, and the mixture was heated to 140 C and reacted for 40 hours. After cooling to room temperature, the mixture was extracted with EA, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. This was subjected to column chromatography with EA: Hx to obtain 12.0 g (Yield = 34%) of [Intermediate 7-1].

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; LG Chem, Ltd.; Gu Gi-dong; Lee Gi-gon; Keum Su-jeong; Yoon Jeong-min; Lee Hyeong-jin; Kim Gong-gyeom; (57 pag.)KR2018/112722; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 1009102-44-6,Some common heterocyclic compound, 1009102-44-6, name is 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, molecular formula is C9H11Cl2N, 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.

[00142] To a solution of (E)-3-((3aS,5aR,5bR,7aR,9S,11aR,11 bR,13aS)-9~hydroxy-1- isopropyI-5a, 5b, 8,8,11a-pentamethyl-2-oxo- 3,3a,4,5,5a,5b,6,7,7a,8,9,10,11 ,11a,11 b,12,13,13a-octadecahydro-2H- cyclopenta[a]chrysen-3a-yl)-2-methylacrylic acid (350 mg, 0.685 mmol), 1-(4- chlorophenyl)cyciopropanamine hydrochloride (154 mg, 0.754 mmol) and HATU (521 mg, 1.371 mmol) in DMF (2 mL) stirred at 0C was added DIPEA (0.479 mL, 2.74 mmol). The reaction mixture was stirred at 20C for 1 h. The reaction mixture was pH adjusted to 3-4 with 2 M HCI and filtered. The solid was washed with water (50 mL), dissolved into DCM, dried over sodium sulfate and evaporated in vacuo to give the crude (E)-N-(1-{4- chlorophenyl)cyclopropyl)-3-((3aS,5aR,5bR,7aR,9S, 1 1 aR, 1 1 bR, 13aS)-9-hydroxy-1 – isopropyl-5a,5b,8,8,11 a-pentamethyl-2-oxo- 3,33,4,5,53,5^6,7,73,8,9, 10,11 ,1 1 a, 1 1 b, 12, 3, 3a-octadecahydro-2H- cyciopenta[a]chrysen-3a-yI)-2-methylacrylamide (650 mg, 0.680 mmol, 99 %) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE LLC; HAN, Nianhe; JOHNS, Brian, A.; TANG, Jun; WO2013/91144; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1009102-44-6, name is 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, belongs to chlorides-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 1009102-44-6, category: chlorides-buliding-blocks

To a solution of the intermediate 16 (10 g, 1 S.5 mmoi), 1 -(4-chlorophenyl) cyclopropanamine hydrochloride (4.15 g, 20.34 mmol), and HATU (14.06 g, 37 mmol) in DMF (35 mL) was added DIPEA (12.92 mL, 74 mmol) at 0 C. The reaction mixture was stirred at room temperature for 1 h. After the pH of the reaction mixture was adjusted to 3-4 with 2 N HCI, the resulting precipitates were collected and washed with water (600 mL). The obtained solid was dissolved in DC , and the solution was dried over sodium sulfate. DCM was removed by rotary evaporation under reduced pressure to provide a crude product, which was taken up in PE/EtOAc/DCM (10/1/1 ) to afford the intermediate 14-6 (1 1 g, 15.16 mmol, 82 %) as a solid. LC/MS: m/z calculated 689.4, found 690.3 (M+1 )+.

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; GLAXOSMITHKLINE LLC; GAO, Daxin; HAN, Nianhe; JOHNS, Brian; JIN, Zhimin; NING, Fangxian; TANG, Jun; WU, Yongyong; YANG, Heping; WO2013/20245; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 450-96-4, 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. 450-96-4, name is 1-Chloro-2-(trifluoromethoxy)benzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Synthesis of INT-41 To a solution of 1-chloro-2-(trifluoromethoxy)benzene (2.5 mmol) in THF (10 mL) is added 2.5 M n-buthyllithium in hexanes (1.4 mmol) at -78 C. After 40 min, a solution of DMF (2.8 mmol) in THF (2.5 mL) is added and the mixture is stirred to room overnight. The reaction is quenched with water at 0 C., extracted with EtOAc (3*50 mL), the combined organic layers are dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography provides 2-chloro-3-(trifluoromethoxy)benzaldehyde (INT-41).

The synthetic route of 1-Chloro-2-(trifluoromethoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tavazoie, Sohail F.; Darst, JR., David M.; Rgenix, Inc.; MARTINEZ, Eduardo J.; KAISER, Bernd; TAVAZOIE, Sohail F; KURTH, Isabel; GONSALVES, Foster Casimir; DARST, David M.; TAVAZOIE, Masoud Fakhr; (106 pag.)US2017/66791; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 90390-33-3, name is 3-Chloro-5-fluorobenzylamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C7H7ClFN

A solution of compound ethyl 2-oxopyrrolidine-3-carboxylate (180.00 g, 929.61 mmol) and (3-chloro-5-fluorophenyl) methanamine (148.36 g, 929.61 mmol) in xylene (4.00 L) is heated to 130 C for 16 hours. LCMS showed the starting material is still present. The reaction mixture is cooled to 10 C and a solid precipitates out after 30 minutes. The suspension is filtered and the filter cake is washed with xylene (3 x500 mL), petroleum ether (2×500 mL), and dried under vacuum to give the desired product (81 g). The filtrates are concentrated under reduced pressure and the residue in xylene (3 L) is heated to 130 C for 40 hours. The reaction mixture is cooled to 10 C and the solid precipitates out after 30 minutes. The suspension is filtered and the filter cake is washed with xylene (2×500 mL), petroleum ether (2×500 mL) and dried in vacuum to give the title product (81.38 g) which is combined with the first lot to give a title product (164.38 g, 607.26 mmol, 65.32% yield) as a white solid. ES/MS m/z 270.9 (M+l).

The synthetic route of 90390-33-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD; HO, Koc Kan; QUAN, Weiguo; ZHOU, Jingye; (51 pag.)WO2018/102256; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 54773-19-2, name is 1,2-Dichloro-3-(trifluoromethyl)benzene, molecular formula is C7H3Cl2F3, 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. category: chlorides-buliding-blocks

500.0 g (2.28 mol, 1.0 eq) of 2,3-dichlorotrifluoromethylbenzene and 50.0 g (0.06 mol, 2.5 mol %) of aqueous 50% CYPHOS (tetradecyltri-n-butylphosphonium chloride) solution are initially charged under nitrogen and heated to 80 C. 990.0 g (2.96 mol, 1.3 eq) of 21% aqueous sodium thiomethoxide solution is metered in at 80 C. over 2 h and the mixture is further stirred at 80 C. for 4 h. The organic phase is drained off and the aqueous phase is extracted with 300 ml of toluene. The combined organic phases are combined and concentrated at 40 C./50 mbar. The residue is distilled under a reduced pressure of 10 mbar. This gives 361 g of a colourless liquid (b.p. 104 C./10 mbar) in a yield of 70%. 1H-NMR (CDCl3, 400 MHz) delta (ppm)=7.67 (dd, J=8.1, 1.3 Hz, 1H), 7.64 (dd. J=8.0, 1.3 Hz, 1H), 7.38 (td, J=8.0, 0.8 Hz, 1H), 2.42 (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 54773-19-2, its application will become more common.

Reference:
Patent; Bayer CropScience Aktiengesellschaft; GALLENKAMP, Daniel; FORD, Mark James; US2019/233382; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics