Month: May 2021

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;,
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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

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. 17601-75-1, name is 2,4-Dichloro-5-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H7Cl2N

Example 21-(2′-Bromo-2′,2′-dichloroethyl)-2,4-dichloro-5-methylbenzene; At room temperature, 7.04 g [0.04 mol] of 2,4-dichloro-5-methylaniline are introduced into 30 ml of 36% aqueous HBr, the mixture is cooled to -10 to -5 C. and a solution, cooled to 0 C., of 3.31 g [0.048 mol] of NaNO2 in 80 ml of water is added dropwise within 60 minutes. Subsequently, the mixture is stirred at -10 to -5 C. for 15 minutes. Subsequently, 1.79 g [0.008 mol] of copper(II) bromide and 6.95 g [0.08 mol] of LiBr are added. To this mixture is added dropwise, at -10 to -5 C. within 30 minutes, a solution of 38.8 g [0.4 mol=10 molar equivalents] of vinylidene chloride in 130 ml of acetone. The mixture is allowed to come to room temperature with good stirring and left to react for another 3 hours. The reaction mixture is diluted with 100 ml of water and extracted twice with 70 ml each time of MTBE. The combined organic phases are washed with 30 ml of water, dried over sodium sulphate and concentrated under reduced pressure. This gives 12.8 g of oil which, according to GC-MS, contains 92 area % of 1-(2′-bromo-2′,2′-dichloroethyl)-2,4-dichloro-5-methylbenzene. This corresponds to a yield of 87.4% of theory.The GC-MS shows, as by-products, 3.3 area % of Sandmeyer product and 1.2 area % of 1-(4-bromo-2′,2′,4′,4′-tetrachlorobutyl)-2,4-dichloro-5-methylbenzene.

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 17601-75-1.

Reference:
Patent; Bayer CropScience AG; US2010/234651; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 914225-61-9, name is 3-Chloro-4-fluoro-5-(trifluoromethyl)aniline, 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. Product Details of 914225-61-9

In a 100 mL round-bottomed flask, di(lH-imidazol-l-yl)methanethione (1.25 g, 7.02 mmol, Eq: 1.5) was combined with CH2CI2 (30 mL) to give a colorless solution. 3-chloro-4- fluoro-5-(trifluoromethyl)aniline (lg, 4.68 mmol, Eq: 1.00) in CH2CI2 (20 mL) was added dropwise at 0C. The reaction was allowed to warm to room temperature, and allowed to stir overnight. Concentrate the solution, the compound was isolated by column chromatography (CH2C12/Hexanes = 80/20) to give the product 0.8 g (67%).

The synthetic route of 3-Chloro-4-fluoro-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BILOTTA, Joseph Anthony; CHEN, Zhi; CHIN, Elbert; DING, Qingjie; ERICKSON, Shawn David; GABRIEL, Stephen Deems; KLUMPP, Klaus; MA, Han; MERTZ, Eric; PLANCHER, Jean-Marc; WEIKERT, Robert James; WO2014/6066; (2014); A1;,
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. 60956-24-3, name is 1,2-Dibromo-4-chlorobenzene, A new synthetic method of this compound is introduced below., Quality Control of 1,2-Dibromo-4-chlorobenzene

Under an argon atmosphere, to a 500 ml, three neck flask, 10.00 g (48.5 mmol) of Intermediate IM-2, 0.84 g (0.03 equiv, 1.5 mmol) of Pd(dba)2, 11.65 g (2.5 equiv, 121.2 mmol) of NaOtBu, 242 ml of toluene, 13.11 g (1 equiv, 48.5 mmol) of 1,2-dibromo-3-chlorobenzene and 0.98 g (0.1 equiv, 4.8 mmol) of tBu3P were added in that order, followed by heating, stirring and refluxing for about 6 hours. After cooling to room temperature, water was added to the reaction product, and an organic layer was separately taken. To an aqueous layer, toluene was added, and an organic layer was extracted once more. The organic layer thus collected was washed with a saline solution and dried with MgSO4. MgSO4 was separated, and the organic layer was concentrated and then, the crude product thus obtained was separated by silica gel column chromatography (using a mixture solvent of hexane and toluene as a developer) to obtain Intermediate IM-4 (11.14 g, yield 73%) as a white solid compound. A molecular ion peak of m/z=314 was observed by measuring FAB-MS, and from the result, the product was identified as Intermediate IM-4.

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; Samsung Display Co., Ltd.; UNO, Takuya; (126 pag.)US2019/372019; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 1298031-94-3, These common heterocyclic compound, 1298031-94-3, name is 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, 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.

8-Bromo-6-chloro-2-methylimidazo[l,2-b]pyridazine (500 mg, 2.0 mmol, prepared according to Example 43) was combined with K2C03 (550 mg, 4.0 mmol) and lH-imidazole (250 mg, 0.36 mmol) in NMP (5 mL). The mixture was stirred at 120 C for 16 h. The mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 0-30% EtOAc in petroleum ether to yield 6-chloro-8-(lH-imidazol-l-yl)-2-methylimidazo[l,2-b]pyridazine (228 mg, 48%). MS m/z 234.0, 236.0 [M+H]+.

The synthetic route of 1298031-94-3 has been constantly updated, and we look forward to future research findings.

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 924818-16-6,Some common heterocyclic compound, 924818-16-6, name is (5-Chloro-2,4-difluorophenyl)methanamine, molecular formula is C7H6ClF2N, 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 80 Preparation of Compound 8Theta (1 R,4S, 12a )-N-(5-chloro-2,4-difluorobenzyl)-7-hydroxy-6,8-dioxo- 1 ,2,3,4,6,8, 12,12a- octahydro-l ,4-methanodipyrido[l ,2-a: r,2′-d]pyrazine-9-carboxamide 80 Step 1 A 50-mL round bottom flask was charged with 80-A (0.12 g, 0.32 mmol), (5-chloro-254-difluorophenyl)methanamme (0.1. 1 g, 0.63 mmol), N,N~ diisopropylethy famine (DIPEA) (0.20 g, 1.58 mmol) and HATU (0.24 g, 0.63 mmol) in EX 1 ( .10 ml). The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated down, re-dissolved in EtOAc (50 raL), washed with saturated NaHCOj (2x), saturated NH4CI and dried over Na2S04. After concentration, the crude was purified by column chromatography on silica gel with hexane-EtOAc to obtain 80-B as a white solid. LCMS-ES ini/z): j VI · i | ; found: 541 .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (5-Chloro-2,4-difluorophenyl)methanamine, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; JIN, Haolun; LAZERWITH, Scott, E.; MARTIN, Teresa, Alejandra, Trejo; BACON, Elizabeth, M.; COTTELL, Jeromy, J.; CAI, Zhenhong, R.; PYUN, Hyung-Jung; MORGANELLI, Philip, Anthony; JI, Mingzhe; TAYLOR, James, G.; CHEN, Xiaowu; MISH, Michael, R.; DESAI, Manoj, C.; WO2014/100323; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics