Category: 933190-51-3

Synthetic Route of 933190-51-3, 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. 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows.

Example XIV(1) 4-((6-((trans-4-aminocyclohexyl)amino)imidazo[1,2-b]pyridazin-8-yl)amino)-N-(2-(4-pyridinyl)ethyl)benzamide (1a) In a 250 ml round bottom flask, under a nitrogen atmosphere, was added 8-bromo-6-chloroimidazo[1,2-b]pyridazine (5.0 g, 18.6 mmol) from Example I(1), step 1b, tert-butyl 4-aminobenzoate (3.95 g, 20.5 mmol), and DMF (30 ml). The solution was cooled to 0 C. and 1.0M potassium tert-butoxide in THF (46 ml) was added drop-wise via syringe over 30 minutes. The reaction was allowed to stir at room temperature for 30 minutes and then warmed to 50 C. for 2 hrs and the concentrated in vacuo to remove THF. The resulting solution was taken up in ethyl acetate and washed with H2O (3*300 ml) and then brine (1*50 ml). The organic layers were combined and dried over Na2SO4 and filtered. Following solvent evaporation, 6.0 g of crude product was obtained. Further purification was done via triteration with 3:1 diethyl ether/heptane to give 2.2 g of tert-butyl 4-(6-chloroimidazo[1,2-b]pyridazin-8-ylamino)benzoate as a brown solid after filtration.

The chemical industry reduces the impact on the environment during synthesis 8-Bromo-6-chloroimidazo[1,2-b]pyridazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/78136; (2007); 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. 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H3BrClN3

To a stirred solution of phenylmethanol (3.35 g, 31 mmol, 1.2 eq) in THF (80 mL), NaH (60% dispersion in mineral oil, 1.34 g, 33.5 mmol, 1.3 eq) is added in portions. The resulting mixture is stirred at RT for 30 min and then 8-bromo-6-chloroimidazo[1,2-b]pyridazine (D-3) (6 g, 25.8 mmol, 1.0 eq) is added. The resulting mixture is stirred at RT for an additional 2 h and then poured into water (30 mL). The mixture is extracted with ethyl acetate (2*100 mL). The combined organic layers are washed with brine, dried over Na2SO4 and filtered. The filtrate is concentrated in vacuo to afford the product, 8-(benzyloxy)-6-chloroimidazo[1,2-b]pyridazine (D-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; Ren, Pingda; Liu, Yi; Li, Liansheng; Chan, Katrina; Wilson, Troy Edward; Castro, Alfredo C.; Evans, Catherine A.; Snyder, Daniel A.; US2012/122838; (2012); 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. 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H3BrClN3

To a solution of 5-ethylpyridin-2-amine (394 mg, 3.23 mmol) in DMF (8 mL) was added NaH (129 mg,60 % dispersion in mineral oil, 3.23 mmol) under N2 atmosphere at room temperature and stirred for another 0.5 h. To this mixture was added 8-bromo-6-chloroimidazo[l,2- b]pyridazine (0.3 g, 1.3 mmol). After 20 h stirring at room temperature, saturated NH4C1 solution was added and the reaction mixture was extracted with ether (200 mL) and washed with water (2 x 50 mL), then brine (2 x 50 mL). After drying and filtration, it was concentrated to afford 6-chloro-N-(5-ethylpyridin-2-yl)imidazo[l,2-b]pyridazin-8-amine (785 mg, crude) as a yellow solid that was used directly without further purification. LC-MS: [M + 1]+ = 274 > tR =1.726 min.

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 933190-51-3.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; KUGLSTATTER, Andreas; LUCAS, Matthew C.; PADILLA, Fernando; WANNER, Jutta; ZHANG, Xiaohu; WO2013/64445; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 933190-51-3, name is 8-Bromo-6-chloroimidazo[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. Safety of 8-Bromo-6-chloroimidazo[1,2-b]pyridazine

A mixture of 8-bromo-6-chloroimidazo[l,2-b]pyridazine (573 mg, 2.47 mmol), 6-(3-tert- butylpyrrolidin-l-yl)pyridin-2-amine (540 mg, 2.47 mmol), Pd2(dba)3 (142 mg, 0.25 mmol), BINAP (307 mg, 0.50 mmol), Cs2C03 (2.4 g, 7.41 mmol) and dioxane (20 mL) was heated to reflux with stirring for 15 h under N2. The solvent was removed in vacuo and the resulting mixture was purified by chromatography (silica gel, 200 – 300 mesh, dichloromethane : MeOH = 50 : 1) to give N-(6-(3-tert-butylpyrrolidin-l-yl)pyridin-2-yl)-6-chloroimidazo [l,2-b]pyridazin- 8-amine (400 mg, crude) as a brown oil. LC-MS: [M+H]+, 371.1 , tR = 2.23 min.

The synthetic route of 8-Bromo-6-chloroimidazo[1,2-b]pyridazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; KUGLSTATTER, Andreas; LUCAS, Matthew C.; PADILLA, Fernando; WANNER, Jutta; ZHANG, Xiaohu; WO2013/64445; (2013); 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 933190-51-3 as follows. Recommanded Product: 8-Bromo-6-chloroimidazo[1,2-b]pyridazine

Step 3a. Preparation of (6-Chloro-imidazo[1,2-b]pyridazin-8-yl)-[5-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amine A mixture of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (214 mg, 921 mumol, Eq: 0.95) and 5-((4-methylpiperazin-1-yl)methyl)pyridin-2-amine (200 mg, 970 mumol, Eq: 1.00) in DMF (10.0 ml) was cooled to 0 C. To this was added sodium hydride (60% in mineral oil, 124 mg, 3.1 mmol, Eq: 3.2). The reaction was allowed to stir at 0 C. for 10 min and then allowed to warm to room temperature and stirred for 72 h. The reaction was quenched with saturated NaHCO3 (aq) and then diluted with water and EtOAc. The organic layer was separated and the aqueous phase was washed with EtOAc. The organic layers were combined, dried over MgSO4 and concentrated in vacuo. The residue was dissolved in Et2O. The organic layer was washed with water and dried over MgSO4. The drying agent was removed by filtration. The resulting solution was concentrated in vacuo to give (6-chloro-imidazo[1,2-b]pyridazin-8-yl)-[5-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amine (170 mg, 49%) as a solid. LC/MS-ESI observed [M+H]+ 358.

According to the analysis of related databases, 933190-51-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; Brotherton-Pleiss, Christine E.; Lopez-Tapia, Francisco Javier; Lou, Yan; US2013/150360; (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. 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 8-Bromo-6-chloroimidazo[1,2-b]pyridazine

0O150] Step 1: To a solution of 8..bromo.-6chioroirnidazo[i,2bjpyridazine (1.0 equiv.) and diethyl 2-methylmalonate (1.0 equiv.) in DMF (0.15 M) was added sodium hydride (2.5 equiv.) at it The reaction was stined for 10 mm, then quenched with saturated ammoniurn chloride and extracted twice with ethyl acetate. The organic phase was dried with magnesium sulfate, filtered and concentrated. The residue was purified via reverse phase prep-1-IPLC to give cliethyl 2-(6-chloroimidazo[i ,2-bpyridazin-8.yI)-2-rnethylmalonate in 21% yield. LCMS (m/z) (M¡ÀH) 326.0, Rt 0.84 miii.

According to the analysis of related databases, 933190-51-3, the application of this compound in the production field has become more and more popular.

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

These common heterocyclic compound, 933190-51-3, name is 8-Bromo-6-chloroimidazo[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. name: 8-Bromo-6-chloroimidazo[1,2-b]pyridazine

Comparative Example 1 e -Bromo-6-chloro-3-iodoimidazo[1 ,2-b]pyridazine A mixture comprising 100 g (430 mmoi) 8-bromo-6-chloroimidazo[1 ,2-b]pyridazine which was prepared according to a procedure described in US2007/78136 (WO2007/38314) , 145 g N-iodosuccinimide, 5 percent per weight cone, hydrochloric acid and 1 L trichloromethane was heated at reflux for 6 hours. 20 g N- iodosuccinimide were added and heating was continued for additional 3 hours. The precipitate was removed and the filtrate was washed with 1 N sodium hydroxide solution, brine and dried over sodium sulfate. After filtration and removal of solvent diisopropyl ether was added and the residue was stirred at 23 C overnight. The precipitate was filtered off and dried to give 66.6 g (43%) of the title compound

The synthetic route of 8-Bromo-6-chloroimidazo[1,2-b]pyridazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; WENGNER, Antje Margret; NEUHAUS, Roland; SIEMEISTER, Gerhard; WO2013/135612; (2013); 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. 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, A new synthetic method of this compound is introduced below., SDS of cas: 933190-51-3

A solution of 6-(trifluoromethyl)pyridin-2-amine (0.668 g, 4.12 mmol) in DMF (5 mL) was added NaH (0.10 g, 4.18 mmol) and stirred for 0.5 h. To the mixture was added 8-bromo-6- chloroimidazo[l,2-b]pyridazine (0.38 g, 1.65 mmol) under N2. The mixture was stirred at room temperature for 16 h then 100 mL of water was added and the precipitate collected by filtration and washed with water to give 6-chloro-N-(6-(trifluoromethyl)pyridin-2-yl)imidazo[l,2- b]pyridazin-8-amine (0.513 g, 99 %) as a light brown solid. LC-MS: [M+H]+, 314.1 , tR = 1.738 min.

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; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; KUGLSTATTER, Andreas; LUCAS, Matthew C.; PADILLA, Fernando; WANNER, Jutta; ZHANG, Xiaohu; WO2013/64445; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, 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 933190-51-3, SDS of cas: 933190-51-3

To a solution of 8-bromo-6-chloroimidazo[l,2-b]pyridazine (1.2 g, 5.16 mmol) in chloroform (30 mL) were added MS (1.161 g, 5.16 mmol) and TFA (0.795 mL, 10.32 mmol). The reaction mixture was stirred at room temperature for 2h and quenched with aHC03. The organic layers were washed with brine and dried over a2S04. The crude product was purified by BIOTAGE (100% CH2C12) to give the product (1.4 g, 76%). XH NMR (400 MHz, CDC13) delta ppm 7.91 (1 H, s), 7.46 (1 H, s); LC/MS: Rt = 2.44 min. LC/MS (Condition A): 357.80/359.80/361.80.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; LIU, Peiying; BALOG, James Aaron; WO2011/137155; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, 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. 933190-51-3.

A mixture of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (1.0 g, 4.3 mmol), 6-(2-methylpyrrolidin-1-yl)pyridin-2-amine (0.84 g, 4.73 mmol), Pd2(dba)3 (0.247 g, 0.43 mmol), BINAP (0.536 g, 0.86 mmol) and Cs2CO3 (4.21 g, 12.9 mmol) in dioxane (30 mL) was heated to 100 C. for 16 h in a sealed tube under N2 atmosphere then concentrated in vacuo. The residue was purified by chromatography (silica gel, 10 g, 200?300 mesh, ethyl acetate:petroleum ether=1:15) to afford 6-chloro-N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (1.2 g, 85%) as a yellow solid. LC-MS: [M+1]+=329, tR=1.930 min.

The synthetic route of 8-Bromo-6-chloroimidazo[1,2-b]pyridazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; Hermann, Johannes Cornelius; Kuglstatter, Andreas; Lucas, Matthew C.; Padilla, Fernando; Wanner, Jutta; Zhang, Xiaohu; US2013/109661; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics