Author: Jessica.F

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

Reference of 16429-44-0, A common heterocyclic compound, 16429-44-0, name is 5-Bromo-3-chlorobenzene-1,2-diamine, molecular formula is C6H6BrClN2, 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 for the synthesis of U3A mixture of U2 (7.2 g, 32.5 mmol) and CDI (6.32 g, 39.0 mmol) in anhydrous THF (100 mL) was refluxed for 16 hours. After cooling to room temperature, the white precipitate was collected by filtration and dried under reduced pressure to afford U3.

The synthetic route of 16429-44-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INSTITUT PASTEUR KOREA; QURIENT CO., LTD.; KIM, Jaeseung; AHN, Seohyun; JEON, Yeejin; PARK, Dongsik; YANG, Young-In; LEE, Doohyung; LEE, SaeYeon; AHN, Jiye; KIM, Jeongjun; NAM, Kiyean; KANG, Sunhee; SEO, MinJung; SEO, Mooyoung; SEO, Jeongjea; HAN, Sung-Jun; KIM, Jung Hwan; LEE, Sangchul; CHOI, Gahee; LEE, Yunmi; (184 pag.)WO2016/16421; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 1298031-94-3, 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 1298031-94-3 as follows.

8-Bromo-6-chloro-2-methyl-imidazo[l,2-b]pyridazine (124 mg, 0.50 mmol) was combined with 3-(lH-pyrazol-l-yl)propan- l-ol (252 mg, 2.0 mmol) and cesium carbonate (650 mg, 2.0 mmol) in CH3CN (4 mL). The mixture was stirred at 40 C for 16 h. To the mixture was added EtOAc (10 mL). The mixture was filtered over Celite. The filtrate was concentrated. The residue was chromatographed on silica gel, eluting with 0- 10% MeOH in EtOAc to yield 6- chloro-2-methyl-8-(3-pyrazol- l-ylpropoxy)imidazo[l,2-b]pyridazine (70 mg, 48%). MS m/z 292.3 [M+H]+.

According to the analysis of related databases, 1298031-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 16429-44-0, A common heterocyclic compound, 16429-44-0, name is 5-Bromo-3-chlorobenzene-1,2-diamine, molecular formula is C6H6BrClN2, 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.

Step 1 : Into a 30 niL vial were charged 5-broino-3-chlorobenzene-l,2- diamine (1.0 equiv), ytterbium (III) trifluoromethanesulfonate (0.1 equiv.) and 1 ,1,1- trimethoxyethane (1.2 equiv.). The mixture was heated at 90 C for 1 h and cooled to room temperature and concentrated in vacuo. The residue was purified by flash chromatography (0-5% MeOH/DCM) to afford 5-broroo-7-chloro-2-methyl-l H-benzo[d]imidazole in 100% yield as a yellow solid. LCMS (m/z) (M+H) = 247.0, 0.81 mm

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; NOVARTIS AG; AVERSA, Robert John; BURGER, Matthew T.; DILLON, Michael Patrick; DINEEN JR., Thomas A.; LOU, Yan; NISHIGUCHI, Gisele A; RAMURTHY, Savithri; RICO, Alice C.; RAUNIYAR, Vivek; SENDZIK, Martin; SUBRAMANIAN, Sharadha; SETTI, Lina Quattrocchio; TAFT, Benjamin R.; TANNER, Huw Rowland; WAN, Lifeng; (307 pag.)WO2016/38582; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 69411-06-9, These common heterocyclic compound, 69411-06-9, name is 4-Chloro-2,6-difluoroaniline, 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 mixture of 24.0 g (147 mmol) of 4-chloro-2,6– difluoroaniline and 22.9 g of 1,2-propanediol was placed in a round bottom flask and heated to 35C with stirring. A mixture of 14.5 g (49 mmol) of 88 percent purity 2-chlorosulfonyl-8-fluoro-5-methoxy[1,2,4]triazolo-[1,5-c]pyrimidine with 29.1 g of dichloromethane was prepared and was added in 1 mL shots over a 4 hour period. The resulting mixture was heated another 4 hours and was then stirred overnight at ambient temperature. It was then cooled to about 20C and filtered, collecting the solids present. The solids were slurried in 30 mL of a 1:1 mix of 2-propanol and water, collected by filtration, washed with 2×30 mL of 2-propanol, and air dried to obtain 14.8 g (75 percent of theory) of the title compound as a white powder of 98 percent purity melting at 203-204C.

The synthetic route of 69411-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; EP1066289; (2003); B1;,
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. 3722-69-8, name is 8-Chlorochroman, A new synthetic method of this compound is introduced below., Computed Properties of C9H9ClO

Step 5: Methyl (iS, 25)-2-(8-chloro-3,4-dihydro-2H- i-benzopyran-6- carbonyl)cyclopropane- 1-carboxylate[00262j Methyl (iS ,2S)-2-(carbonochloridoyl)cyclopropane- 1 -carboxylate (0.19 g, 1.19 mmol) in DCE (2 mL) was added portionwise to a cooled (0 C), stirred solution of aluminium trichloride (0.32 g, 2.37 mmol) in DCE (4 mL) under a nitrogen atmosphere. 8-Chloro-3,4-dihydro-2H- 1 -benzopyran (0.2 g, 1.19 mmol) was added dropwise over 5 minutes and the reaction mixture was stirred at 0 C for a further 1 hour. After this time, the mixture was allowed to warm to room temperature before being stirred overnight. The reaction mixture was then cooled to 0 C before being added portionwise to a mixture of concentrated HC1 (4 mL) and ice (20 g). The resulting mixture was then extracted with DCM (3 x 50 mL), the combined organic extracts were washed with brine (30 mL), before being dried (MgSO4), filtered and concentrated. The resulting residue was purified using a Biotage Isolera, (Snap 50 g cartridge, eluting in 0-45 % EtOAc in Heptanes) to give the title compound (0.15 g, 43% yield) as a pale yellow oil. oH (250 MHz, CDC13) 7.88 (d, J= 2.1 Hz, 1H), 7.69- 7.62 (m, 1H), 4.43 -4.31 (m, 2H), 3.73 (s, 3H), 3.08 (ddd, J= 8.5, 5.9, 3.8 Hz, 1H), 2.86 (t, J 6.4 Hz, 2H), 2.36 (ddd, J 8.5, 6.1, 3.8 Hz, 1H), 2.16 – 1.96 (m, 2H), 1.58 (tdd, J= 7.6, 5.9, 3.4 Hz, 2H). Tr = 2.00 mm m/z (ESj (M+Hj295.

The synthetic route of 3722-69-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHDI FOUNDATION, INC.; TOLEDO-SHERMAN, Leticia, M; DOMINGUEZ, Celia; PRIME, Michael; MITCHELL, William, Leonard; JOHNSON, Peter; WENT, Naomi; WO2013/151707; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics