Category: pyridazine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5469-69-2,3-Amino-6-chloropyridazine,as a common compound, the synthetic route is as follows.

To a solution of 3-amino-6-chloropyridazine (19.2 g,148 mmol; CASNo. 5469-69-2) in EtOH (500 mL) was added 10% Pd catalyst on 1940 carbon (unreduced, 55% water). Triethylamine (50 mL) was added and the mixture was hydrogenated under 500 psi/mole for 1.9 h. The reaction was filtered and the ethanol was washed with aqueous NH4CI. The organic layer was concentrated to give pyridazin-3-amine as a white solid (11 g, 78% yield). MS (APCI 10V) AP+1 96.2. To a suspension of pyridazin-3-amine (5 g, 50 mmol) in THF (50 mL) and CH3CN (70 mL) was added pyridine (5.10 mL, 63.1 mmol) followed by phenyl chloroformate (6.95 mL, 55.2 mmol) slowly. The reaction was stirred overnight. The reaction was filtered to remove the precipitate. The filtrate was concentrated and then taken up in CH2CI2 which was washed with water. The organic layer was dried using SPE phase separators and concentrated. The residue was purified by silica gel column chromatography (0-5% MeOH/CH2CI2). An undesired side product eluted first followed by the title compound which was concentrated to give a white solid (7.5 g, 70% yield). MS (APCI 10V) AP+1 216.12; 1H NMR (400 MHz, DMSO-d6) delta ppm 7.20 – 7.24 (m, 2 H) 7.25 – 7.28 (m, 1 H) 7.39 – 7.44 (m, 2 H) 7.64 – 7.69 (m, 1 H) 8.05 (dd, 1 H) 8.94 (dd, 1 H) 11.34 (s, 1 H).

As the paragraph descriping shows that 5469-69-2 is playing an increasingly important role.

Reference£º
Patent; PFIZER INC.; WO2009/127949; (2009); A1;,
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6082-66-2, 3,4,6-Trichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

3-Chlorobenzo[5, 6] [1, 4] dioxino[2, 3-c] pyridazine (51) To a suspension of sodium hydride (15.0 g, 375.0 mmol) in 1, 4-dioxane (400 mL) was added benzene-1, 2-diol (36.0 g, 320.0 mmol) and 3, 4, 6-trichloropyridazine (60.0 g, 320.0 mmol) under the ice-bath. The resulting solution was stirred at 100 C. for 10 h before quenched by the addition of saturated NaCl(aq) (100 mL). The resulting solution was extracted with ethyl acetate (3*500 mL) and the organic layers combined. Then the organic layer was washed with brine. The mixture was dried over anhydrous sodium sulfate and filtered. The residue was purified by flash column chromatography with ethyl acetate/petroleum ether (1:3) to afford 3-chlorobenzo[5, 6][1, 4] dioxino[2, 3-c] pyridazine (51) as a white solid (32.0 g, 50%). ESI-MS, m/z=221 [M+H]+.

The synthetic route of 6082-66-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Tsai, Guochuan Emil; Wang, Ching-Cheng; Hsieh, Yuan-Ting; (53 pag.)US2019/112289; (2019); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.932-22-9,4,5-Dichloro-3(2H)-pyridazinone,as a common compound, the synthetic route is as follows.

Synthesis of 4.5-dichloro-2-((3-chloropyridin-4-yl”)methyl”)pyridazin-3(2HVone (G3-1″) 30 G3-1 To a solution of compound 4 (200 mg, 1.21 mmol), compound 30 (235 mg, 1.45 mmol) and K2C03 (335 mg, 2.42 mmol) in DMF (3 mL) was added KI (20 mg, 0.12 mmol). The solution was stirred at 90 C for 2h. The mixture was cooled to room temperature and quenched with water, extracted with EtOAc for 3 times, combined the organic layer, washed with brine, dried over Na2S04, filtered, concentrated under reduced pressure, purified by HPLC to give G3-1 (135 mg, 47%) as a brown solid. NMR (DMSO-(3?6, 300 MHz): delta 5.40 (s, 2H), 7.23 (d, J= 5.1 Hz, 1H), 8.31 (s, 1H), 8.47 (d, J = 4.8 Hz, 1H), 8.67 (s, 1H); LCMS [mobile phase: 20-95% Acetonitrile +0.02% NH40Ac] purity is >95%, Rt = 3.163 min; MS 291; MS Found: 292 (M+l)+.

932-22-9 4,5-Dichloro-3(2H)-pyridazinone 73247, apyridazine compound, is more and more widely used in various.

Reference£º
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; BECKWITH, Jonathan Roger; DUTTON, Rachel; ESER, Markus; LANDETA, Cristina; BLAZYK, Jessica L.; MEEHAN, Brian M.; HATAHET, Feras; BOYD, Dana; WO2015/143164; (2015); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.84956-71-8,2-(tert-Butyl)-4,5-dichloropyridazin-3(2H)-one,as a common compound, the synthetic route is as follows.

Synthesis of 2-tert-Butyl-4-chloro-5-thio-3(2H)-pyridazinone To 0.5 g of 2-tert-Butyl-4,5-dichloro-3(2H)-pyridazinone was added 7 ml water and sodium sulfide (0.53 g, 6.81 mmol) and the mixture was heated to 80 C. until all the solid dissolved. The solution was then cooled to room temperature and concentrated HCl was carefully added to give a yellow precipitate, which was filtered and washed with cold water. Crystallization from hexanes afforded the product as a white solid (270 mg).

As the paragraph descriping shows that 84956-71-8 is playing an increasingly important role.

Reference£º
Patent; Casebier, David S.; Robinson, Simon P.; Purohit, Ajay; Radeke, Heike S.; Azure, Michael T.; Dischino, Douglas D.; US2005/191238; (2005); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.34584-69-5,3,6-Dichloro-4,5-dimethylpyridazine,as a common compound, the synthetic route is as follows.

Step a. To a solution of 3,6-dichloro-4,5-dimethylpyridazine (CAS Number 34584-69-5, available from Accela chembio) (6 g, 33.9 mmol) in CC14 (150 ml) were added NBS (18.08 g, 101.6 mmol) and AIBN (0.055 g, 0.33 mmol) at rt. The reaction mixture was heated at 80¡ãC for 16 h. The resulting reaction mixture was filtered and evaporated to yield 4,5-bis(bromomethyl)-3,6-dichloropyridazine (11 g, 32.8 mmol), LCMS: Method A, 2.102 min, MS: ES+ 335.18.

As the paragraph descriping shows that 34584-69-5 is playing an increasingly important role.

Reference£º
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
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372118-01-9, Methyl 4,6-dichloropyridazine-3-carboxylate is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound 4,6-dichloropyridazine-3-carboxylic acid methyl ester 1a (581 mg, 2.81 mmol),4-morpholinoaniline 92c (500mg, 2.81mmol),Diisopropylethylamine (3.63 g, 28 mmol) and acetonitrile (10 mL) were mixed, heated to 90 C and stirred for 18 hours.After cooling to room temperature, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 100/0 to 1/4),The target product 6-chloro-4-((4-morpholinophenyl) amino) pyridazine-3-carboxylic acid methyl ester 92d (768 mg, brown solid) was obtained in a yield of 78%.

The synthetic route of 372118-01-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Beijing Nuochengjianhua Pharmaceutical Technology Co., Ltd.; Chen Xiangyang; Pang Yucheng; (142 pag.)CN110818641; (2020); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1632-76-4,3-Methylpyridazine,as a common compound, the synthetic route is as follows.

A solution of 3-Methylpyridazine 15 (5.0 g, 53.0 mmol) in THF (10 mL) was added to potassium tert-butoxide (8.9 g, 80.0 mmol) in THF (50 mL) at 0 C. After stirring at room temperature for 1.5 hours, tert-butyl nitrite (12.6 mL, 106 mmol) in THF (10 mL) was added to the reaction mixture at 0 C. After stirring at room temperature for 19 hours, the solvent was removed in vacuo and the residue was added to 4 M HCl solution (20 mL). The resulting mixture was concentrated in vacuo and filtered a colorless powder of aldoxime 16a (1.8 g). The residue was extracted with ethylacetate (50 mL 3). The organic layer was dried over MgSO4. The solvent was removed in vacuo, then triturated with n-hexane to yield aldoxime 16a (2.8 g). The combined aldoxime 16a (4.6 g, 71%) was E, Z mixture of isomer. N-Chlorosuccimide (4.0g, 30 mmol) was added to a suspension of 16a (3.7 g, 30 mmol), ethynyl tri-n-butylstannane (9.3 g, 20 mmol), NaHCO3 (6.3 g, 75 mmol), ethyacetate (100 mL) and distilled water (5 mL). After stirring at room temperature for 16 hours, distilled water (5 mL) was added to the reaction mixture. After stirring at room temperature for 4 hours, the reaction mixture was washed with saturated NaHCO3 (100 mL), and the aqueous layer was extracted with ethylacetate (100 mL). The combined organic layer was dried over MgSO4. The solvent was removed in vacuo and the residue was used in the next reaction without further purification. The crude 17a was dissolved in THF (100 mL). Iodine (3.2 g, 25.2 mmol) was added to the solution at room temperature. After stirring at room temperature for 35 minutes, the reaction mixture was diluted with 6% sodium thiosulfate solution (100 mL) and extracted with ethylacetate (100 ml). The organic layer was washed with brine and dried over MgSO4. The solvent was removed in vacuo and the residue was recrystallized from n-hexane to yield compound 14a (2.9 g, 35% for two steps) as a brown powder

1632-76-4 3-Methylpyridazine 74208, apyridazine compound, is more and more widely used in various.

Reference£º
Article; Sugimoto, Tomohiro; Shimazaki, Yoichi; Manaka, Akira; Tanikawa, Tetsuya; Suzuki, Keiko; Nanaumi, Kayoko; Kaneda, Yoshie; Yamasaki, Yukiko; Sugiyama, Hiroyuki; Bioorganic and Medicinal Chemistry Letters; vol. 22; 17; (2012); p. 5739 – 5743;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1837-55-4,3,5-Dichloropyridazine,as a common compound, the synthetic route is as follows.

A mixture of 3,5-dichloropyridazine(l .00 g, 6.71 mmol) and liquid Nfb was stirred in a sealed tube for 12 h. A black residue was formed. The residue was purified by Combi Flash (50% to 100% EtOAc in pentane) to give 5-chloropyridazin-3-amine (400 mg, yield: 44%) as a yellow solid. (1582) NMR (400 MHz DMSO-rie) d 6.66 (1H, d, J= 2.3 Hz), 6.84 (2H, brs), 8.50 (1H, d, J= 2.3 Hz).

The synthetic route of 1837-55-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PETRA PHARMA CORPORATION; KESICKI, Edward A.; LINDSTROeM, Johan; PERSSON, Lars Boukharta; VIKLUND, Jenny; FORSBLOM, Rickard; GINMAN, Tobias; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (391 pag.)WO2019/126730; (2019); A1;,
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187973-60-0, 6-Iodopyridazin-3-amine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Reference Example 3 Production of ethyl (6-iodoimidazo[1,2-b]pyridazin-2-yl)carbamate To a solution of 3-amino-6-iodopyridazine (27.0 g, 122 mmol) in N,N-dimethylacetamide (270 mL) were added ethyl (chloroacetyl)carbamate (32.4 g, 195 mmol) and disodium hydrogenphosphate (43.4 g, 305 mmol), and the mixture was stirred at 110 C. for 3 hr. After cooling the mixture to room temperature, water (810 mL) was added, and the precipitated crystals were filtrated, and washed with acetonitrile and ether to give the title compound (33.0 g, 81%) as a dark brown powder. 1H-NMR (DMSO-d6, 300 MHz) delta 1.26 (3H, t, J=7.1 Hz), 4.17 (2H, q, J=7.1 Hz), 7.47 (1H, d, J=9.2 Hz), 7.70 (1H, d, J=9.2 Hz), 8.06 (1H, s), 10.51 (1H, brs).

187973-60-0 6-Iodopyridazin-3-amine 10867834, apyridazine compound, is more and more widely used in various.

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/137595; (2009); A1;,
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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

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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