Downstream synthetic route of 29049-45-4

29049-45-4, 29049-45-4 6-Chloropyridazin-4-amine 14099144, apyridazine compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.29049-45-4,6-Chloropyridazin-4-amine,as a common compound, the synthetic route is as follows.

To a stirred suspension of potassium tert-butoxide (7.80 g, 69.5 mmol) inl,4-Dioxane (50 mL) was added (R)-(2,2-dimethyl-l,3-dioxolan-4-yl)methanol (5.20 mL, 41.7 mmol) at 0 C and the reaction mixture was stirred at 25 C for 1 h. under Nitrogen atmosphere. Then 6-chloropyridazin-4-amine (3 g, 23.16 mmol) was added to the reaction mixture and the resulting reaction mixture was stirred at 1 10 C for 16 h. (TLC System Ethyl acetate, Rf: 0.3). The reaction mixture was poured into ice cold water (40 ml) and extracted with EtOAc (2×80 mL). The combined organic layer was washed with brine solution (50 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to get crude compound. The crude product was purified by flash column chromatography (Neutral alumina, Eluent: 65% Ethyl acetate in Pet ether) to afford the desired product (R)- 6-((2,2-dimethyl-l,3-dioxolan-4-yl)methoxy)pyridazin-4-amine (2.2 g, 9.66 mmol, 41.7 % yield) as an off white solid. LCMS (m/z): 226.05 [M+H]+, Rt = 1.00 min.

29049-45-4, 29049-45-4 6-Chloropyridazin-4-amine 14099144, apyridazine compound, is more and more widely used in various fields.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ELLIS, James Lamond; EVANS, Karen Anderson; FOX, Ryan Michael; MILLER, William Henry; SEEFELD, Mark Andrew; (766 pag.)WO2016/79709; (2016); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

Downstream synthetic route of 29049-45-4

29049-45-4 6-Chloropyridazin-4-amine 14099144, apyridazine compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.29049-45-4,6-Chloropyridazin-4-amine,as a common compound, the synthetic route is as follows.

Synthesis of 5-bromo-3-chloropyridazine. To a solution 6-chloropyridazin-4-amine (2 g, 15 mmol), t-BuONO (2.4 g, 23 mmol) in MeCN (40 mL) was added CuBr2 (5 g, 23 mmol) at 0 C. The resulting mixture was stirred at RT for 16 h and then concentrated in vacuo. The mixture was diluted with EtOAc (50 mL) and added H2O (50 mL). After filtered through celite, the filtrate was extracted with EtOAc (50 mL*3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give the crude product which was purified by silica gel chromatography (PE/EA=20/1) to give 5-bromo-3-chloropyridazine (1.32 g, yield: 43%) as a brown oil. ESI-MS [M+H]+: 192.8, 194.8., 29049-45-4

29049-45-4 6-Chloropyridazin-4-amine 14099144, apyridazine compound, is more and more widely used in various fields.

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

Analyzing the synthesis route of 29049-45-4

29049-45-4, As the paragraph descriping shows that 29049-45-4 is playing an increasingly important role.

29049-45-4, 6-Chloropyridazin-4-amine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred suspension of potassium tert-butoxide (3.90 g, 34.7 mmol) in 1,4-Dioxane (50 mL) was added a mixture of (,S)-(2,2-dimethyl-l,3-dioxolan-4-yl)methanol (2.75 g, 20.84 mmol) at 0 C and the reaction mixture was stirred at 25 C for 1 h. under Nitrogen atmosphere, then 6-chloropyridazin-4-amine (1.5 g, 1 1.58 mmol) was added to the reaction mixture and the resulted reaction mixture was stirred at 1 10 C for 16 h. (TLC System: Neat Ethyl acetate, Rf: 0.3). The reaction mixture was poured in to ice cold water (40 ml) and extracted with EtOAc (2×80 mL). The combined organic layer was washed with brine solution (50 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to get crude compound. The crude material was purified by flash column chromatography (Neutral alumina, Eluent: 65% Ethyl acetate in Pet ether) to afford the desired product (,S)-6-((2,2-dimethyl-l,3-dioxolan-4-yl)methoxy)pyridazin-4-amine (1.0 g, 4.28 mmol, 37.0 % yield) as a white solid. LCMS (m/z): 226.20 [M+H]+.

29049-45-4, As the paragraph descriping shows that 29049-45-4 is playing an increasingly important role.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ELLIS, James Lamond; EVANS, Karen Anderson; FOX, Ryan Michael; MILLER, William Henry; SEEFELD, Mark Andrew; (766 pag.)WO2016/79709; (2016); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

New learning discoveries about 29049-45-4

29049-45-4 6-Chloropyridazin-4-amine 14099144, apyridazine compound, is more and more widely used in various fields.

29049-45-4, 6-Chloropyridazin-4-amine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0512] Compound 487A was prepared by an analogous method as that of 473B, except using compound 3-chloro-5-aminopyridazine in place of compound 2-bromo-6-aminopyridine., 29049-45-4

29049-45-4 6-Chloropyridazin-4-amine 14099144, apyridazine compound, is more and more widely used in various fields.

Reference:
Patent; Das, Jagabandhu; Padmanabha, Ramesh; Chen, Ping; Norris, Derek J.; Doweyko, Arthur M.P.; Barrish, Joel C.; Wityak, John; Lombardo, Louis J.; Lee, Francis Y.F.; US2004/54186; (2004); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

New learning discoveries about 29049-45-4

29049-45-4 6-Chloropyridazin-4-amine 14099144, apyridazine compound, is more and more widely used in various fields.

29049-45-4, 6-Chloropyridazin-4-amine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

29049-45-4, Into a 50-mL round-bottom flask, was placed 6-chloropyridazin-4-amine (570 mg, 4.40 mmol, 1 equiv), dioxane (20 mL), CH3NH2-H20 (4 mL). The resulting solution was stirred overnight at 140 C. The resulting mixture was concentrated under vacuum. The crude product was purified by Flash-Prep-HPLC A. This resulted in 320 mg (59%) of the title compound as a yellow solid. Analytical Data: LC-MS: (ES, m/z): RT= 0.187 min, LCMS 45, m/z = 125 [M+l].

29049-45-4 6-Chloropyridazin-4-amine 14099144, apyridazine compound, is more and more widely used in various fields.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; FOLEY, Megan Alene; HARVEY, Darren Martin; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (586 pag.)WO2017/181177; (2017); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

Analyzing the synthesis route of 29049-45-4

As the paragraph descriping shows that 29049-45-4 is playing an increasingly important role.

29049-45-4, 6-Chloropyridazin-4-amine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A suspension of 4-amino-6-chloropyridazine (1) (2.59 g, 22.3 mmol, 1.0 eq) in CH2CI2 (65 ml_) was cooled to 0 C before the addition of triethylamine (10.9 ml_, 77.9 mmol, 3.5 eq) and di-fe/f-butyl dicarbonate (12.2 g, 55.7 mmol, 2.5 eq). The suspension was warmed to room temperature and stirred for 17.5 h then DMAP (277 mg, 2.23 mmol, 0.1 eq) and additional di-fe/f-butyl dicarbonate (4.86 g, 22.3 mmol, 1.0 eq) were added. The reaction was stirred for 2.5 h then concentrated in vacuo. Purification twice by silica gel chromatography using hexane/EtOAc (1 :0-4: 1 ) yielded intermediate 2 as an orange solid (3.40 g, 46%). (1299) LCMS (ES): Found 174.0 [M-C02fBu-fBu+3H]+. (1300) 1H NMR (300MHz, DMSO-cf6), d: 9.33 (d, J=2.1 Hz, 1 H), 8.14 (d, J=2.1 Hz, 1 H), 1.41 (s, 18H)., 29049-45-4

As the paragraph descriping shows that 29049-45-4 is playing an increasingly important role.

Reference:
Patent; KARUS THERAPEUTICS LIMITED; SHUTTLEWORTH, Stephen Joseph; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; ALEXANDER, Rikki Peter; SILVA, Franck; CECIL, Alexander; (233 pag.)WO2019/166824; (2019); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

Simple exploration of 29049-45-4

The synthetic route of 29049-45-4 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.29049-45-4,6-Chloropyridazin-4-amine,as a common compound, the synthetic route is as follows.

29049-45-4, General procedure: A mixture of 4-chloropyridin-2-amine (64 g, 498 mmol), phenyl boronic acid (61 g, 500 mmol), Na2CO3 (159 g, 1.5 mol), Pd(PPh3)4 (6.4 g) in H20/EtOH/toluene (500 mL) was heated to 90 C in sealed vessel for 14 h. The crude mixture was cooled, filtered, and concentrated under reduced pressure. Purification (FCC, 5i02,PE:EtOAc (100:1) afforded the title Compound (64 g, 75%).

The synthetic route of 29049-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ARORA, Nidhi; BACANI, Genesis M.; BARBAY, Joseph Kent; BEMBENEK, Scott D.; CAI, Min; CHEN, Wei; DECKHUT, Charlotte Pooley; EDWARDS, James P.; GHOSH, Brahmananda; KREUTTER, Kevin; LI, Gang; TICHENOR, Mark S.; VENABLE, Jennifer D.; WEI, Jianmei; WIENER, John J. M.; WU, Yao; XIAO, Kun; ZHANG, Feihuang; ZHU, Yaoping; (528 pag.)WO2017/100662; (2017); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

Some tips on 29049-45-4

The synthetic route of 29049-45-4 has been constantly updated, and we look forward to future research findings.

29049-45-4, 6-Chloropyridazin-4-amine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step C: N-(6-Chloro-4-pyridazinyl)-N’-(1-methylethyl)urea To a stirred solution of 0.8 gram of 4-amino-6-chloro-pyridazine in 30 ml of dimethylformamide is added 0.2 gram of 1,4-diazabicyclo[2.2.2]octane, followed by 0.6 gram of 1-methylethyl isocyanate. The reaction mixture is stirred at ambient temperature for 18 hours, then at 60 C. for six hours. The majority of the dimethylformamide is removed under reduced pressure, and the residue is slurried in water. The resultant solid is collected by filtration and dried to yield N-(6-chloro-4-pyridazinyl)-N’-(1-methylethyl)urea., 29049-45-4

The synthetic route of 29049-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FMC Corporation; US4728355; (1988); A;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

Downstream synthetic route of 29049-45-4

29049-45-4, 29049-45-4 6-Chloropyridazin-4-amine 14099144, apyridazine compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.29049-45-4,6-Chloropyridazin-4-amine,as a common compound, the synthetic route is as follows.

To a stirred suspension of potassium tert-butoxide (7.80 g, 69.5 mmol) inl,4-Dioxane (50 mL) was added (R)-(2,2-dimethyl-l,3-dioxolan-4-yl)methanol (5.20 mL, 41.7 mmol) at 0 C and the reaction mixture was stirred at 25 C for 1 h. under Nitrogen atmosphere. Then 6-chloropyridazin-4-amine (3 g, 23.16 mmol) was added to the reaction mixture and the resulting reaction mixture was stirred at 1 10 C for 16 h. (TLC System Ethyl acetate, Rf: 0.3). The reaction mixture was poured into ice cold water (40 ml) and extracted with EtOAc (2×80 mL). The combined organic layer was washed with brine solution (50 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to get crude compound. The crude product was purified by flash column chromatography (Neutral alumina, Eluent: 65% Ethyl acetate in Pet ether) to afford the desired product (R)- 6-((2,2-dimethyl-l,3-dioxolan-4-yl)methoxy)pyridazin-4-amine (2.2 g, 9.66 mmol, 41.7 % yield) as an off white solid. LCMS (m/z): 226.05 [M+H]+, Rt = 1.00 min.

29049-45-4, 29049-45-4 6-Chloropyridazin-4-amine 14099144, apyridazine compound, is more and more widely used in various fields.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ELLIS, James Lamond; EVANS, Karen Anderson; FOX, Ryan Michael; MILLER, William Henry; SEEFELD, Mark Andrew; (766 pag.)WO2016/79709; (2016); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

Downstream synthetic route of 29049-45-4

29049-45-4 6-Chloropyridazin-4-amine 14099144, apyridazine compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.29049-45-4,6-Chloropyridazin-4-amine,as a common compound, the synthetic route is as follows.

Synthesis of 5-bromo-3-chloropyridazine. To a solution 6-chloropyridazin-4-amine (2 g, 15 mmol), t-BuONO (2.4 g, 23 mmol) in MeCN (40 mL) was added CuBr2 (5 g, 23 mmol) at 0 C. The resulting mixture was stirred at RT for 16 h and then concentrated in vacuo. The mixture was diluted with EtOAc (50 mL) and added H2O (50 mL). After filtered through celite, the filtrate was extracted with EtOAc (50 mL*3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give the crude product which was purified by silica gel chromatography (PE/EA=20/1) to give 5-bromo-3-chloropyridazine (1.32 g, yield: 43%) as a brown oil. ESI-MS [M+H]+: 192.8, 194.8., 29049-45-4

29049-45-4 6-Chloropyridazin-4-amine 14099144, apyridazine compound, is more and more widely used in various fields.

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem