Analyzing the synthesis route of 19064-67-6

19064-67-6, As the paragraph descriping shows that 19064-67-6 is playing an increasingly important role.

19064-67-6, 6-Chloro-3-hydroxypyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 255 2-benzyl-6-chloro-2H-pyridazine-3-one 6-chloro-2H-pyridazine-3-one (3.50 g) was dissolved in DME (130 mL). To this solution, cesium carbonate (17.5 g) was added and the mixture was stirred at room temperature for 15 min in an argon atmosphere. Subsequently, benzyl bromide (4.00 mL) was added and the mixture was stirred at room temperature for 3.5 hours. The insoluble inorganic residue was removed by filtration and the filtrate was concentrated. Water was then added to the residue and the mixture was extracted with ethyl acetate, washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated and the resulting crystals were recrystallized from ethyl acetate/petroleum ether to afford the title compound as a pale yellow powder (4.94 g). 1H NMR (200 MHz, CDCl3) delta 7.28-7.47 (5H, m), 7.15 (1H, d, J=9.6 Hz), 6.90 (1H, d, J=9.6 Hz), 5.25 (2H, s). 13C NMR (50 MHz, CDCl3) delta 158.77, 137.43, 135.48, 133.66, 132.20, 128.86, 128.67, 128.20, 55.43

19064-67-6, As the paragraph descriping shows that 19064-67-6 is playing an increasingly important role.

Reference£º
Patent; Kohno, Yasushi; Adams, David Roger; Ando, Naoki; US2008/207902; (2008); A1;,
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Brief introduction of 19064-67-6

19064-67-6, As the paragraph descriping shows that 19064-67-6 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19064-67-6,6-Chloro-3-hydroxypyridazine,as a common compound, the synthetic route is as follows.

To a solution of 6-chloropyridazin-3(2H)-one (0.35 g, 2.68 mmol) in DMF (10 mL) was added K2CO3 (0.93 g, 6.70 mmol) and methyl iodide (0.20 mL, 3.22 mmol). The resulting mixture was stirred at 25 C for 1 h. To the reaction mixture was added ice cold water (30 mL) and the mixture was extracted with ethyl acetate (2 x 50 ml). The combined organic layers were washed with brine (30 mL), dried over sodium sulfate and distilled under reduced pressure to obtain Intermediate 107 (0.25 g, 56.10%) as an off white solid.1H NMR (400 MHz, CDCl3) delta ppm 3.75 (s, 3 H), 6.92 (d, J = 9.76 Hz, 1 H), 7.19 (d, J = 9.76 Hz, 1 H). LCMS (Method-D): retention time 0.66 min, [M+1] 145.2.

19064-67-6, As the paragraph descriping shows that 19064-67-6 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; PANDA, Manoranjan; YADAV, Navnath Dnyanoba; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (321 pag.)WO2018/93569; (2018); A1;,
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Pyridazine | C4H4N2 – PubChem

 

Some tips on 19064-67-6

The synthetic route of 19064-67-6 has been constantly updated, and we look forward to future research findings.

19064-67-6, 6-Chloro-3-hydroxypyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A) 6-Chloro-2-(2-dimethylamino-ethyl)-2H-pyridazin-3-one:To a solution of 6-chloro-pyridazin-3-one (500 mg, 3.83 mmol) in 5 mL N,N- dimethylformamide was added 2-dimethylaminoethyl chloride hydrochloride (828 mg, 5.75 mmol), potassium carbonate (1.59 g, 11.5 mmol) and sodium iodide (632 mg, 4.21 mmol). The mixture was stirred over night at 65 0C. The solvent was evaporated. The crude product was purified by preparative HPLC using a gradient of acetonitrile / 5 % acetonitrile-water phase containing 0.1 M ammonium acetate, to give 174 mg of the desired sub-title product as light brown solids after freeze drying (22 % yield). 1H NMR (400 MHz, methanol-d4 as solvent and internal reference) delta (ppm) 2.35 (s, 6H), 2.82 (t, 2H, J = 6.4 Hz), 4.26 (t, 2H, J = 6.5 Hz), 6.9S (d, IH, J = 9.7 Hz), 7.44 (d, IH. J = 9.7 Hz)., 19064-67-6

The synthetic route of 19064-67-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTRAZENECA AB; WO2007/8144; (2007); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

Downstream synthetic route of 19064-67-6

19064-67-6 6-Chloro-3-hydroxypyridazine 252828, apyridazine compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19064-67-6,6-Chloro-3-hydroxypyridazine,as a common compound, the synthetic route is as follows.

To a 250-mL round-bottom flask was placed a solution of 6- chloro-2,3-dihydropyridazin-3-one (1.87 g, 14.33 mmol) and 2-chloro-N-[4- (trifluoromethyl)phenyl]propanamide (3 g, 11.92 mmol, as prepared in the previous step) in acetone (60 mL) then K2CO3 (4.9 g, 35.20 mmol) was added. The reaction was stirred at 60C for 16 h, then the solids were filtered out and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography eluting with EtO Ac/petroleum ether (1:20 up to 1: 1) affording 1.4 g (34%) of the title compound as a white solid. Mass Spectrum (LCMS, ESI pos): Calcd. for (0182) Ci4H12ClF3N302+: 346.1 (M+H); Found: 346.1. H NMR (300 MHz, DMSO-cfe): delta 10.62 (s, 1H), 7.80-7.77 (d, / = 8.4 Hz, 2H), 7.70-7.62 (m, 3H), 7.12-7.08 (d, / = 9.9 Hz, 1H), 5.43-5.34 (q, / = 7.2 Hz, 1H), 1.61-1.59 (d, / = 7.2 Hz, 3H)., 19064-67-6

19064-67-6 6-Chloro-3-hydroxypyridazine 252828, apyridazine compound, is more and more widely used in various.

Reference£º
Patent; PROTEOSTASIS THERAPEUTICS, INC.; PARKS, Daniel; MUNOZ, Benito; (66 pag.)WO2018/81378; (2018); A1;,
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Pyridazine | C4H4N2 – PubChem

 

Downstream synthetic route of 19064-67-6

19064-67-6 6-Chloro-3-hydroxypyridazine 252828, apyridazine compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19064-67-6,6-Chloro-3-hydroxypyridazine,as a common compound, the synthetic route is as follows.

Step 1: 6-(2,4-Dichloro-phenylsulfanyl)-2H-pyridazin-3-one. Potassium t-butoxide (1.1 g) was added to a solution of 2,4-dichlorothiophenol (1.8 g) in N,N-dimethylformamide (DM F) (5 mL). The mixture was stirred at room temperature for 10 minutes and then 6-chloro 2H-pyridazin-3-one (1.31 g) was added. The reaction mixture was stirred at 100 C. for five hours. The mixture was then cooled to room temperature, poured into water (20 mL) and 20% potassium hydroxide (5 mL) was added. The resulting dark solution was extracted with ethyl acetate (2*10 mL). The aqueous layer was collected and the pH was adjusted to 3 with concentrated hydrochloric acid. The solution was then extracted with ethyl acetate (3*10 mL). The ethyl acetate layer was collected, dried over anhydrous sodium sulfate, filtered and evaporated to obtain a crude product, which was purified by silica gel chromatography (1:1 ethyl acetate/hexane as eluent) to afford 6-(2,4-dichloro-phenylsulfanyl)-2H-pyridazin-3-one (418 mg, 15%); NMR 6.88 (d, 1H), 7.10 (d, 1H), 7.24 (dd, 1H), 7.48 (d, 11H), 7.52 (d, 1H).

19064-67-6 6-Chloro-3-hydroxypyridazine 252828, apyridazine compound, is more and more widely used in various.

Reference£º
Patent; Martin, William H.; Mylari, Banavara L.; US2003/4139; (2003); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

Analyzing the synthesis route of 19064-67-6

As the paragraph descriping shows that 19064-67-6 is playing an increasingly important role.

19064-67-6, 6-Chloro-3-hydroxypyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6-Chloro-2H-pyridazin-3-one (944 mg, 7.23 mmol) and difluoro(fluorosulfonyl)acetic acid (1.42 g, 7.96 mmol) were dissolved in acetonitrile (19 ml) in a vessel with stirrer bar and stirred at room temperature for 40 h. The reaction solution was then diluted with ethyl acetate (150 ml) and washed successively with water, saturated sodium hydrogencarbonate solution and again with water. The organic phase was dried using sodium sulfate, filtered and evaporated to dryness in a rotary evaporator. The residue was taken up in cyclohexane, re-filtered, and the solvent was removed in a rotary evaporator. The residue obtained was purified by means of flash column chromatography (gradient cyclohexane/0-50% by vol. of ethyl acetate, CombiFlash Rf 200). The suitable product fractions were combined, and the solvents were removed in a rotary evaporator, giving 3-chloro-6-(difluoromethoxy)pyridazine (285 mg, 1.58 mmol, MS: 181.0/183.1[M+H+]), 22% yield) as colourless liquid.

As the paragraph descriping shows that 19064-67-6 is playing an increasingly important role.

Reference£º
Patent; Merck Patent GmbH; FUCHSS, Thomas; EMDE, Ulrich; BUCHSTALLER, Hans-Peter; MEDERSKI, Werner; (224 pag.)US2016/83401; (2016); A1;,
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Pyridazine | C4H4N2 – PubChem

 

Analyzing the synthesis route of 19064-67-6

As the paragraph descriping shows that 19064-67-6 is playing an increasingly important role.

19064-67-6, 6-Chloro-3-hydroxypyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound 2 (2.1 g, 16 mmol) was dissolved in N,N-dimethylformamide.Add cesium carbonate (10.4 g, 32 mmol),Methyl 4-bromomethylbenzoate (3.7 g, 16 mmol),Stir at room temperature and continue to stir the reaction.TLC detects the progress of the reaction,The reaction was complete after 4 hours.Add appropriate amount of ethyl acetate and dilute the extract.Washed with saturated saline,The organic phase is concentrated,Separated and purified by silica gel column chromatography (ethyl acetate / petroleum ether = 1/3).4.0 g of a white solid compound 3 was obtained in a yield of 90%.

As the paragraph descriping shows that 19064-67-6 is playing an increasingly important role.

Reference£º
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Hu Youhong; Geng Meiyu; Duan Wenwen; Ding Jian; Wan Penghui; Shen Aijun; Lu Dong; Liu Hongchun; Wei Aihuan; Zhang Minmin; Zeng Limin; Cao Jingchen; (57 pag.)CN109280032; (2019); A;,
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Pyridazine | C4H4N2 – PubChem