Category: 933190-51-3

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., name: 8-Bromo-6-chloroimidazo[1,2-b]pyridazine

A mixture of 8-bromo-6-chloroimidazo[l ,2-b]pyridazine (1.0 g, 4.3 mmol), 6-(2- methylpyrrolidin-l-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 Cs2C03 (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-l-yl)pyridin-2-yl)imidazo[l ,2-b]pyridazin- 8- amine (1.2 g, 85 %) as a yellow solid. LC-MS: [M + l]+ = 329 > tR =1.930 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;,
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Electric Literature of 933190-51-3, The chemical industry reduces the impact on the environment during synthesis 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, I believe this compound will play a more active role in future production and life.

Preparation of 6-chloro-N-cyclopropylimidazo[1,2-b]pyridazin-8-amine To a solution of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (1.00 g, 3.21 mmol, 1.0 equiv) and p-TSA (611 mg, 3.21 mmol, 1.0 equiv) in DMSO (10.0 mL) was added cyclopropylamine (1.13 mL, 16.1 mmol, 5.0 equiv) and heated to 100 C. for 24 h. Purification by column chromatography using 50% ethyl acetate in hexanes elution gave 536 mg of the white solid, 80%.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Califia Bio, Inc.; GOODFELLOW, VAL S.; NGUYEN, THONG X.; RAVULA, SATHEESH B.; GELBARD, HARRIS A.; US2014/256733; (2014); A1;,
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Synthetic Route of 933190-51-3, 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.

General procedure: To a solution of 6a-6c (1 mmol) in THF (5 mL) was addedmorpholine (or (S)-3-methylmorpholine, or 8-oxa-3-azabicyclo[3.2.1]octane) (1.2 mmol) and Et3N (2.2 mmol). The mixture washeated under reflux for 12 h. The crude product was extracted with CH2Cl2, dried over Na2SO4, purified over silica gel chromatographyeluting with PE and EtOAc to give 7a-7g [43].

Statistics shows that 8-Bromo-6-chloroimidazo[1,2-b]pyridazine is playing an increasingly important role. we look forward to future research findings about 933190-51-3.

Reference:
Article; Mao, Beibei; Gao, Shanyun; Weng, Yiran; Zhang, Liangren; Zhang, Lihe; European Journal of Medicinal Chemistry; vol. 129; (2017); p. 135 – 150;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 933190-51-3,Some common heterocyclic compound, 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, 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 8-bromo-6-chloroimidazo[l,2-b]pyridazine (300 mg, 1.3 mmol), (S)-6-(2- methylpyrrolidin-l-yl)pyridin-2-amine (252 mg, 1.42 mmol), Pd2(dba)3 (75 mg, 0.13 mmol), BINAP (324 mg, 0.52 mmol), Cs2C03 (1272 mg, 3.9 mmol) and dioxane (20 mL) was heated to 100 C with stirring for 16 h under N2. The solvent was removed in vacuo and the resulting mixture was purified by chromatography (silica gel, 200 – 300 mesh, petroleum ether : ethyl acetate = 3 : 1) to give (S)-6-chloro-N-(6-(2-methylpyrrolidin-l-yl)pyridin-2-yl)imidazo [1,2- b]pyridazin-8-amine (124 mg, 29 %) as a yellow solid. LC-MS: [M+H]+, 329.0, tR = 1.95 lmin.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, its application will become more common.

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

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

Intermediate 1-13To a suspension of Intermediate 1-12 (950 mg, 4.08 mmol) and Cs2C03 (1.6 g, 4.9 mmol) in acetonitrile (20 mL) was added allyl alcohol (0.3 mL, 4.5 mmol). The reaction mixture was heated at 65C for 6 h. More Cs2C03 (1.0 g) and allyl alcohol (0.25 mL) were added and the mixture was stirred at rt overnight. Water was added and the mixture was extracted with EtOAc. The organic phase was washed with brine, dried, filtered and concentrated. The residue was purified by column chromatography (cHex:EtOAc 2:1 to 1 :1.5) to give Intermediate 1-13 (690 mg, 80%).HPLC-MS (method 4): Rt =3.32 min, [M+Hf 210.H NMR (300 MHz, CDCI3) delta 7.87 (d, J = 0.9 Hz, 1H), 7.68 (s, 1H), 6.43 (s, 1 H), 6.13 (ddd, J = 22.7, 10.8, 5.5 Hz, 1H), 5.54 (d, J = 16.3 Hz, 1H), 5.44 (d, J = 10.4 Hz, 1H), 4.89 (d, J = 5.5 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 933190-51-3, its application will become more common.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); SNODIN, Michael D; PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALEZ, Sonia; BLANCO-APARICIO, Carmen; LORENZO GARCIA, Milagros; RAMOS LIMA, Francisco Javier; WO2013/5041; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 933190-51-3,Some common heterocyclic compound, 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, 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 8-bromo-6-chloroimidazo[l,2-]pyridazine (340 mg, 1.463 mmol) (prepared as described by Vaccaro W. et al. United States Patent Appl. US 2008/0045536 Al, 2008) and N-(4-methoxybenzyl)aniline (312 mg, 1.46 mmol) in THF (5 mL) at 0 C was added LiHMDS (4.39 mL, 4.39 mmol, 1 M in THF). The reaction mixture was stirred at 0 C for 3 h. The starting material was still present. Additional LiHMDS (4.39 mL, 4.39 mmol, 1 M in THF) was added and the reaction was stirred at room temperature for 2 h. LCMS indicated complete consumption of the starting material. The reaction mixture was transferred to a separatory funnel containing saturated aqueous NaHC03 solution (25 mL) and the aqueous layer was extracted with EtOAc (3 x 25 mL). The combined organic layers were concentrated and the residue was purified by column chromatography on silica gel (10%? 30% ethyl acetate in hexanes) to afford 6-chloro-N-(4-methoxybenzyl)-N- phenylimidazo[l,2-£]pyridazin-8-amine (280 mg, 53%> yield) as a yellow solid: LRMS (ESI) mle 365.2 [(M + H)+, calcd for C2oHi8N4OCl 365.2].

The synthetic route of 933190-51-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; AHUJA, Vijay T.; RAJAMANI, Ramkumar; DZIERBA, Carolyn Diane; BRONSON, Joanne J.; MACOR, John E.; WO2015/26574; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 933190-51-3, 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. 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

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[1,2-b]pyridazine (0.3 g, 1.3 mmol). After 20 h stirring at room temperature, saturated NH4Cl solution was added and the reaction mixture was extracted with ether (200 mL) and washed with water (2×50 mL), then brine (2×50 mL). After drying and filtration, it was concentrated to afford 6-chloro-N-(5-ethylpyridin-2-yl)imidazo[1,2-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.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

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

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. Safety of 8-Bromo-6-chloroimidazo[1,2-b]pyridazine

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 104a (2.0 g, 4 mmol), 5-(4-methylpiperazin-1-yl)pyridin-2-amine (920 mg, 4.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (366 mg, 0.4 mmol), XantPhos (688 mg, 1.2 mmol), Cs2CO3 (2.6 g, 8.0 mmol), and 1,4-dioxane (60 mL). After three cycles of vacuum/argon flush, the mixture was heated at reflux for 15 h. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica-gel column chromatography eluting with dichloromethane/methanol (20:1) to afford 104b as yellow solid (1.4 g, 70%). MS: [M+H]+344.

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; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Young, Wendy B.; US2013/116262; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 933190-51-3, 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. 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1. Preparation of (6-Chloro-imidazo[1,2-b]pyridazin-8-yl)-[5-(4-isopropyl-piperazin-1-yl)-pyridin-2-yl]-amine A mixture of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (200 mg, 862 mumol, Eq: 0.95) and 5-(4-isopropylpiperazin-1-yl)pyridin-2-amine (200 mg, 908 mumol, Eq: 1.00) in DMF (10.0 ml) was cooled to 0 C. To this reaction mixture was added sodium hydride (116 mg, (60% in mineral oil), 2.9 mmol, Eq: 3.2). The reaction was allowed to stir at 0 C. for 10 min then allowed to warm to room temperature and stir 18 h. The reaction mixture was quenched with sat. NaHCO3 (aq) and diluted with water and EtOAc. The organic layer was separated and the aqueous phase was extracted with EtOAc. The organic layers were combined, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 0% to 20% (60:10:1 DCM:MeOH:NH4OH)/DCM gradient) to give a residue that was placed under high vacuum for 18 h to afford (6-chloro-imidazo[1,2-b]pyridazin-8-yl)-[5-(4-isopropyl-piperazin-1-yl)-pyridin-2-yl]-amine (78 mg, 23%). LC/MS-ESI observed [M+H]+ 372.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

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

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

Benzyl alcohol (0.3 mL, 2.98 mmol) was dissolved in tetrahydrofuran (40 mL) under nitrogen and cooled to 0 C in an ice water bath. Sodium hydride (0.25 g) was added and the solution was stirred at 0 for 30 min. 8-bromo-6-chloroimidazo[1,2-b]pyridazine (462 mg, 1.99 mmol) in tetrahydrofuran (50 mL) was added dropwise and the mixture was slowly returned to room temperature and stirred for 1 h.The reaction was quenched with saturated sodium chloride solution (50 mL), extracted with ethyl acetate (500 mL), washed with organic phase (50 mL) and saturated sodium chloride solution (50 mL), dried over anhydrous sodium sulfate, concentrated under reduced pressure and the residue was subjected to column chromatography (V (ethyl acetate) / V (petroleum ether) = 1/2) to give 0.26 g of an oily product in a yield of 50%.

The synthetic route of 933190-51-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CHENG, CHANGCHUNG; ZHANG, YINGJUN; LIU, BING; LONG, BOHUA; CHEN, YU; CHENG, ZHIXIN; (202 pag.)TW2017/6256; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics