Category: 19064-67-6

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 (1.5 g, 12 mmol) was dissolved in water.Add liquid bromine (1.8 mL, 36 mmol),Potassium bromide (4.3 g, 36 mmol),After potassium acetate (1.76 g, 18 mmol),Heated to reflux,TLC was used to detect the progress of the reaction.The reaction was stirred overnight.The reaction is complete,Add appropriate amount of ethyl acetate and dilute the extract.Washed with saturated saline,The organic phase is concentrated,Separation and purification by silica gel column chromatography (ethyl acetate / petroleum ether = 1/2).1.76 g of a white solid compound 8 was obtained in a yield of 71%.

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

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;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

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 256 6-chloro-2-(pyridine-3-ylmethyl)-2H-pyridazine-3-one 6-chloro-2H-pyridazine-3-one (1.00 g) was dissolved in DMF (76 mL). To this solution, 60% sodium hydride (370 mg) was added at room temperature in an argon atmosphere and the mixture was vigorously stirred at 50 C. Meanwhile, 60% sodium hydride (370 mg) was added to a solution of 3-(chloromethyl)pyridine hydrochloride (1.51 g) in DMF at -40 C. in an argon atmosphere and the solution was allowed to warm to room temperature. Using a cannula, this solution was poured into the pyridazinone solution and the mixture was stirred first at 50 C. for 90 min and then at room temperature for 18 hours. Subsequently, a saturated ammonium chloride solution was added and the solvent was concentrated. Water was then added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent and subsequent purification by silica gel column chromatography (ethyl acetate: petroleum ether=7:3, followed by methanol:ethyl acetate=5:95) afforded the title compound as a colorless powder (1.30 g). 1H NMR (200 MHz, CDCl3) delta 8.70 (1H, d, J=1.5 Hz), 8.55 (1H, dd, J=4.8, 1.5 Hz), 7.78 (1H, dt, J=7.9, 1.5 Hz), 7.26 (1H, dd, J=7.9, 4.9 Hz), 7.16 (1H, d, J=9.6 Hz), 6.90 (1H, d, J=9.6 Hz), 5.24 (2H, s). 13C NMR (50 MHz, CDCl3) delta 158.63, 150.17, 149.62, 137.82, 136.64, 133.91, 132.17, 131.07, 123.54, 52.95, 19064-67-6

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

Reference£º
Patent; Kohno, Yasushi; Adams, David Roger; Ando, Naoki; US2008/207902; (2008); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

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 1000-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 6-chloro-2,3- dihydropyridazin-3-one (5 g, 38.30 mmol) and (3-methoxyphenyl)boronic acid (7.6 g, 50.01 mmol) in dioxane (300 mL)/water (15 mL) then Pd(dppf)Cl2 (1.41 g) and K2C03 (15.9 g, 115.04 mmol) were added. The reaction was stirred at 110C for 15 h, quenched by the addition of 100 mL of water, and extracted with EtOAc (3×150 mL). The organic extracts were combined, washed with brine (3×200 mL), dried over anhydrous Na2S04, and concentrated under reduced pressure. The residue was purified by column chromatography eluting with EtO Ac/petroleum ether (9: 1) affording 5.6 g (72%) of the title compound as a white solid. Mass Spectrum (LCMS, ESI pos): Calcd. for CnHnN202+: 203.1 (M+H); Found: 203.1., 19064-67-6

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

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

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 B. To a solution of 6-chloro-2H-pyridazin-3-one (500 mg, 3.83 mmol) in 5 mL 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 C. Solvent was evaporated. The crude product was dissolved in water and purified by preparative HPLC using a gradient of acetonitrile/5 % acetonitrile-water phase containing 0.1 M ammonium acetate, to give 174 mg of 6-chloro-2- (2-dimethylamino-ethyl)-2H-pyridazin-3-one as light brown crystals 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), 4.26 (t, 2H), 6.98 (d, 1H), 7.43 (d, 1H).

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

Reference£º
Patent; ASTRAZENECA AB; WO2005/65688; (2005); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

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.

Compound 2 (2 mmol),4-methoxycarbonylbenzeneboronic acid (2 mmol),Copper acetate (0.4 mmol),Pyridine (0.4 mmol) in the reaction flask,Add 15 mL of DMF and dissolve at room temperature with stirring.Open reaction for about 4 hours,The reaction was complete by TLC.Add appropriate amount of ethyl acetate for extraction.Washed with saturated saline,The organic phase is concentrated,Separation and purification by silica gel column chromatography (ethyl acetate /Petroleum ether = 1/3),Obtained 2.1 g of white solid compound 25,The yield was 80%.

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; 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;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

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.

General procedure: A suspension of 3,6-dichloropyridazine (25.50 g, 171.2 mmol) in 100 mL of water was treated with NaOH (15.06 g, 376.6 mmol) and heated at 80 C for 2 h. The resulting red solution was allowed to cool to rt and was then acidified to pH 1 with concentrated HCl (aq). The off-white solid was washed with water and Et2O and then dried under vacuum overnight to afford 6-chloropyridazin-3(2H)-one (4, 19.13 g,85% yield). A mixture of 4 (2.55 g, 19.54 mmol) and EtI (1.88 mL, 23.44 mmol) in 10 mL of DMF at rt was treated with K2CO3 (8.10 g, 58.61 mmol). The reaction mixture stirred 48 h at rt and then H2O was added and the mixture was extracted with EtOAc. The combined organic layers were washed with water, dried over Na2SO4, filtered and concentrated to give 6-chloro-2-ethylpyridazin-3(2H)-one (5, 2.70 g, 87% yield). A solution of 5 (2.70 g, 17.03 mmol) in hydrazine hydrate (4.14 mL, 85.13 mmol) was heated at 70 C. After 2 h, the reaction mixture was loaded directly on to a silica gel column and eluted with 0-10% MeOH in CH2Cl2 to afford 2-ethyl-6-hydrazinylpyridazin-3(2H)-one (6, 1.26 g, 48% yield) as a light-yellow solid. A mixture of 6 (163 mg, 1.06 mmol) and 2-chloro-6-fluorobenzaldehyde (168 mg, 1.06 mmol) in 8 mL of EtOH was heated to reflux. After 1 h, the reaction mixture was concentrated, the solid wasresuspended in THF (8 mL) and chloramine T-hydrate (265 mg, 1.16 mmol) was added. The mixture was heated at 65 C for 4 h. The reaction mixture was allowed to cool to rt and H2O was added. The mixture was extracted with EtOAc. The combined organic layers were dried over anhydrous Na2SO4,filtered and concentrated. The crude material was purified by silica gel chromatography (0-50% EtOAc in hexanes) to afford 3-(2-chloro-6-fluorophenyl)-5-ethyl-[1,2,4]triazolo[4,3-b]pyridazin-6(5H)-one (7, 222 mg, 72% yield). A mixture of 7 (222 mg, 0.76 mmol) and Br2 (0.19 mL, 3.79 mmol) in 3 mL of acetic acid was heated at 80 C for 2 h. The reaction was cooled to rt, water was added and the mixture was extracted with EtOAc. The combined organic layers were washed with H2O and saturated NaHCO3 (aq) and then dried over anhydrous Na2SO4, filtered and concentrated to afford 7,8-dibromo-3-(2-chloro-6-fluorophenyl)-5-ethyl-7,8-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-6(5H)-one (8, 285 mg, 83% yield) as a yellow oil. A solution of 8 (285 mg, 0.63 mmol) in 3 mL of THF at rt was treated with NEt3 (0.26 mL, 1.89 mmol). After 1 h, H2O was added and the mixture was extracted with EtOAc. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to give 7-bromo-3-(2-chloro-6-fluorophenyl)-5-ethyl-[1,2,4]triazolo[4,3-b]pyridazin-6(5H)-one (9, 194 mg, 83% yield) as a yellow oil. In a microwave tube was placed 9 (194 mg, 0.52 mmol), 10 (190 mg, 0.63 mmol), PdCl2(PPh3)2 (18 mg, 0.026 mmol) and 2 M Na2CO3 (aq, 1.3 mL, 2.6 mmol) and 2.5 mL of dioxane. The mixture was heated in a microwave at 120 C for 25 min. After cooling to rt, H2O was added and the mixture was extracted with EtOAc. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The crude material was purified by HPLC (Phenomenex 150 x 30 mm Luna column) eluting with 5-100% CH3CN in water with 0.1% TFA at 35 mL/min over 15 min to afford 3-(3-(2-chloro-6-fluorophenyl)-5-ethyl-6-oxo-5,6-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-7-yl)-N-cyclopropyl-4-methylbenzamide (3j, 69 mg, 28% yield) as an off-white solid.

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

Reference£º
Article; Herberich, Brad; Jackson, Claire; Wurz, Ryan P.; Pettus, Liping H.; Sherman, Lisa; Liu, Qiurong; Henkle, Bradley; Saris, Christiaan J.M.; Wong, Lu Min; Chmait, Samer; Lee, Matthew R.; Mohr, Christopher; Hsieh, Faye; Tasker, Andrew S.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 2; (2012); p. 1226 – 1229;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

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 mixture of 6-chloropyridazin-3 (2H)-one (0.140 g, 1.07 mmol), (3 -methylquinolin-7-yl)boronic acid, (0.221 g, 1.18 mmol), Cu(OAc)2 (0.0390 g, 0.215 mmol) and pyridine(0.191 ml, 2.36 mmol) in DCM (10.7 mL, 1.07 mmol) was stirred at room temperature overnight. The reaction mixture was partitioned between EtOAc and water. The organic extracts were washed with brine, then dried over anhydrous Na2SO4(), filtered and concentrated under vacuum. The resulting residue was purified by silica chromatography to afford the title compound (25 mg, 8.6% yield). MS (apci) m/z = 274.0 [(M+H)+2], 272.0 (M+H) with Cl pattern.

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

Reference£º
Patent; ARRAY BIOPHARMA, INC.; ANDREWS, Steven W.; BLAKE, James F.; COOK, Adam; GUNAWARDANA, Indrani W.; HUNT, Kevin W.; METCALF, Andrew T.; MORENO, David; REN, Li; TANG, Tony P.; (263 pag.)WO2017/70708; (2017); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

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.

General procedure: Method A. A mixture of corresponding chloronitropyridine (Ia-c) (1.59 g, 10 mmol), diazole or 3-chloropyridazin-6-one (10 mmol), and powdered K2CO3 (4.14 g) was thoroughly stirred for several hours at a temperature from 45 to 65 C (the exact time and temperature values are shown for the individual compound). The mixture was then cooled, poured into 100 mL of H2O, and the formed precipitate was filtered off and washed with water.

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

Reference£º
Article; Klimenko; Divaeva; Zubenko; Morkovnik; Fetisov; Bodryakov; Russian Journal of Bioorganic Chemistry; vol. 41; 4; (2015); p. 402 – 408; Bioorg. Khim.; vol. 41; 4; (2015); p. 454 – 461,8;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

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 A 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 (DMF) (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 (2X10 mL). The aqueous layer was collected and the pH was adjusted to 3 with concentrated hydrochloric acid. The solutionwas then extracted with ethyl acetate (3X10 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,1H), 7.52 (d,1H).

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; Pfizer Products Inc.; EP1260224; (2002); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

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 mixture of 6-chloropyridazin-3(2H)-one (0.200 g, 1.53 mmol), (3-cyano- 5-methoxyphenyl)boronic acid (0.298 g, 1.69 mmol), Cu(OAc)2 (0.0557 g, 0.306 mmol) and pyridine (0.273 mL, 3.37 mmol) in DCM (9.58 mL) was stirred overnight at ambient temperature. The mixture was then diluted with DCM and extracted with water and brine, then dried over anhydrous Na2SO4(), filtered and concentrated under vacuum. The resulting crude residue was purified by silica chromatography to afford the title compound (197 mg, 49% yield). ?H NIVIR (CDC13) 7.60 (t, 1H), 7.49 (t, 1H), 7.28 (d, 1H), 7.18 (m, 1H), 7.40(d, 1H), 3.88 (s, 3H)., 19064-67-6

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

Reference£º
Patent; ARRAY BIOPHARMA, INC.; ANDREWS, Steven W.; BLAKE, James F.; COOK, Adam; GUNAWARDANA, Indrani W.; HUNT, Kevin W.; METCALF, Andrew T.; MORENO, David; REN, Li; TANG, Tony P.; (263 pag.)WO2017/70708; (2017); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem