Heterocyclic Building Blocks-Pyridazine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14161-11-6,3,4,5-Trichloropyridazine,as a common compound, the synthetic route is as follows.

A mixture of of 3 ,4,5-trichloropyridazine (0.276 g, 1.506 mmol), 4-(3 -fluorophenyl)piperidine (0.27 g, 1.506 mmol), and potassium carbonate (0.437 g, 3.16 mmol) in dioxane (10 ml) was heated to reflux for 1 h. The mixture was cooled and 35% hydrazine (2.73 ml, 30.1 mmol) was added. The mixture was heated to reflux for an additional 16 h.The reaction was diluted with ethyl acetate and water. The ethyl acetate layer waswashed with water, dried over magnesium sulfate, and concentrated to give 4-chloro-5-(4-(3 -fluorophenyl)piperidin- 1 -yl)-3 -hydrazinylpyridazine (0.25 g, 52%). LCMS:Rt = 1.940 mm, 26%, (M-H) = 320, (M+H) = 322., 14161-11-6

As the paragraph descriping shows that 14161-11-6 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; MATTSON, Ronald J.; MENG, Zhaoxing; GUERNON, Leatte R.; WO2013/192306; (2013); A1;,
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141-30-0, 3,6-Dichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,141-30-0

Example 2. 6-4-f4- (5-Chloro-lH-indole-2-sulphonyl)-piperazine-l-carbonvl]-phenyl}-2- (2-dimethylamino-ethvl)-2H-pyridazin-3-one Step A. To a microwave vial was added 3,6-dichloropyridazine (645mg, 4.33mmol), potassium acetate (425 mg, 4.33 mmol) and 9 mL acetic acid/water (5: 1). The reaction mixture was heated at 140 C for 70 minutes. The solvent was evaporated and the crude was purified by preparative HPLC using a gradient of acetonitrile/5 % acetonitrile- water phase containing 0.1 M ammonium acetate, to give 436 mg of 6-chloro-2H- pyridazin-3-one (77 % yield). 1H NMR (400 MHz ; methanol-d4 as solvent and internal reference) delta (ppm) 6.96 (d, 1H), 7.45 (d, 1H).

As the paragraph descriping shows that 141-30-0 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; WO2005/65688; (2005); A1;,
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88497-27-2,88497-27-2, 3-Amino-6-bromopyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of ethyl 4-chloro-3-oxobutanoate (1.99 g, 811.49 mmol) and 6-bromopyridazin-3 -amine (1.0 g, 6.90 mmol, PharmaBlock) in EtOH (15 mL) was heated in a microwave at 120 C for 2 h. The reaction was concentrated under reduced pressure. The residue was dissolved in EtOAc (about 250 mL) and washed with water, sat. sodium bicarbonate, and then brine. The organics were collected, dried over MgS04, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica (EtOAc /heptane 0-50 %) to give the title compound (1.06 g, 65%) LC/MS (Table 1, Method i) = 0.73 min; MS m/z: 284, 286 (M+H)+ .

As the paragraph descriping shows that 88497-27-2 is playing an increasingly important role.

Reference£º
Patent; ABBVIE INC.; BREINLINGER, Eric, C.; COX, Phil, B.; DAANEN, Jerome; DIETRICH, Justin; DJURIC, Stevan; DOMBROWSKI, Amanda, W.; FRANK, Kristine, E.; FRIEDMAN, Michael, M.; GOMTSYAN, Arthur; LI, Huan-Qui; LONGENECKER, Kenton; OSUMA, Augustine; ROWLEY, Ann, Marie; SCHMIDT, Robert; VASUDEVAN, Anil; WILSON, Noel; (378 pag.)WO2016/168641; (2016); A1;,
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38956-79-5, 3-Hydrazinyl-6-methylpyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 C for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 C for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 ¡Á 25 mL), dried over anhydrous sodium sulfate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7 (See reference no; 7 for supporting information).

38956-79-5, As the paragraph descriping shows that 38956-79-5 is playing an increasingly important role.

Reference£º
Article; Ruso, Jayaraman Sembian; Rajendiran, Nagappan; Srinivas, Chowdappa; Murthy, Konappa Narasimha; Soumya, Krishnamurthy; Journal of the Korean Chemical Society; vol. 58; 4; (2014); p. 377 – 380;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.187973-60-0,6-Iodopyridazin-3-amine,as a common compound, the synthetic route is as follows.

General procedure: Method H: to a solution of compound 12a (788 mg, 3.24 mmol)in n-butanol (12 mL) was added compound 3 (717 mg, 3.24 mmol).The mixture was refluxed for 16 h, evaporated to dryness, and theresidue was suspended in CHCl3. The solution was made alkalinewith a 30% ammonium hydroxide solution and extracted withCHCl3. The combined organic layers were dried over MgSO4,filtered, and evaporated under reduced pressure to give the desiredimidazo[1,2-b]pyridazine 13a (1.20 g, 100%) as a brown solid., 187973-60-0

The synthetic route of 187973-60-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Moine, Esperance; Dimier-Poisson, Isabelle; Enguehard-Gueiffier, Cecile; Loge, Cedric; Penichon, Melanie; Moire, Nathalie; Delehouze, Claire; Foll-Josselin, Beatrice; Ruchaud, Sandrine; Bach, Stephane; Gueiffier, Alain; Debierre-Grockiego, Francoise; Denevault-Sabourin, Caroline; European Journal of Medicinal Chemistry; vol. 105; (2015); p. 80 – 105;,
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932-22-9, 4,5-Dichloro-3(2H)-pyridazinone is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of dichloropyridazinone (50.0 g, 303.0 mmol) in DMF (200 mL) was added K2CO3 (50.3 g, 364.0 mmol) at RT under vigorous stirring. Benzylbromide (40.0 mL, 336.0 mmol) was added in rapid drops via a syringe. The resulting suspension was stirred at 50 C. for 1 h until all the pyridazinone was consumed as judged by HPLC. The reaction mixture was then poured into water (400 mL). The resultant suspension was stirred for 15 min at RT, and then filtered. The collected solid was rinsed thoroughly with water until no color was apparent in the filtrate. The solid was dried in a vacuum oven at 50 C. overnight to give the title compound, 2-benzyl-4,5-dichloropyridazin-3(2H)-one, (73.1 g, 95%) as pale yellow solid. HPLC: 3.17 min; MS, M+H=255., 932-22-9

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

Reference£º
Patent; Yu, Guixue; Ewing, William R.; Mikkilineni, Amarendra B.; Pendri, Annapurna; Sher, Philip M.; Gerritz, Samuel; Ellsworth, Bruce A.; Wu, Gang; Huang, Yanting; Sun, Chongqing; Murugesan, Natesan; Gu, Zhengxiang; Wang, Ying; Sitkoff, Doree; Johnson, Stephen R.; Wu, Ximao; US2005/143381; (2005); A1;,
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5788-58-9, 4,5-Dibromopyridazin-3(2H)-one is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,5788-58-9

To a stirred solution of (2R)-2-methyl-1-[(2-methylphenyl)methyl]piperazine (400 mg, 1.96 mmol, 1 equiv.) and DIEA(506.1 mg, 3.92 mmol, 2 equiv.) in DMA(5 mL) was added 4,5- dibromo-2,3-dihydropyridazin-3-one (596.5 mg, 2.35 mmol, 1.200 equiv.) in portions at 100 degrees C overnight. The reaction liquid was purified by Prep-HPLC with the following conditions (Column: XBridge Prep C18 OBD Column 19X150mm 5um; Mobile Phase A: Water(10 mmol/L NH4HCO3), Mobile Phase B: MeCN; Flow rate: 20 mL/min; Gradient: 40% B to 60% B in 9 min; 254/220 nm; Rt: 8.45 min) to afford 4-bromo-5-[(3R)-3-methyl-4-[(2- methylphenyl)methyl]piperazin-1-yl]-2,3-dihydropyridazin-3-one (18.7mg,2.53%) as a white solid.

5788-58-9 4,5-Dibromopyridazin-3(2H)-one 236181, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
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33471-40-8, 4-Methylpyridazin-3(2H)-one is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The product of step c) (12.2 g, 0.112 mol) in phosphorus oxychloride (125 ML) was heated at 90C for 3 h. The mixture was cooled to room temperature and concentrated almost to dryness. The residue was poured into ice/water, made basic by careful addition of 4N NAOH and extracted with ether. The aqueous phase was re-extracted with DCM. The organic phases were combined, washed with water, dried over sodium sulphate, filtered and concentrated to dryness. The residue was purified by flash chromatography on silica gel in 2: 1 ethyl acetate- isohexane to give an orange solid (11.2 g, 78%). LH NMR (400 MHz, CDCIs) 8 8.97 (1 H, d, J = 4. 9 HZ), 7.35 (1 H, d, J = 4. 9 HZ), 2.44 (3 H, s) ppm., 33471-40-8

33471-40-8 4-Methylpyridazin-3(2H)-one 11412358, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP & DOHME LIMITED; WO2004/74290; (2004); A1;,
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Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1121-79-5,3-Chloro-6-methylpyridazine,as a common compound, the synthetic route is as follows.

2 M Aqueous Na2CO3 solution (1.13 ml.) is added to a mixture of (2R.6R, 11 S)-6, 11 -dimethyl- 8-(4.4.5.5-tetramethyl-[1 .3.2]dioxaborolan-2-yl)-1 .2.5.6-tetrahydro-4H-2,6-methano- benzo[d]azocine-3-carboxylic acid tert-butyl ester (483 mg) and 3-chloro-6-methyl-pyridazine (218 mg) in dimethylformamide (2 ml_). The resulting mixture is flushed with argon and then 1 ,1 ‘-bis(diphenylphosphino)ferrocene-palladium dichloride dichloromethane complex (73 mg) is added. The mixture is heated to 100 0C and stirred at this temperature overnight. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined organic extracts are washed with water and brine and dried (MgSO4). The solvent is removed under reduced pressure and the residue is taken up in CH2CI2 (3 ml.) and treated with F3CCO2H (0.5 ml.) for 1 h. Then, the solution is concentrated and the residue is purified by HPLC on reversed phase (MeCN/H2O/NH3) to afford the title compound.Yield: 225 mg (68% of theory) Mass spectrum (ESI+): m/z = 294 [M+H]+, 1121-79-5

1121-79-5 3-Chloro-6-methylpyridazine 227254, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/63061; (2009); A2;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.20744-39-2,Pyridazin-4-amine,as a common compound, the synthetic route is as follows.

General procedure: To a solution of 17c (100mg, 0.34mmol) in 5mL anhydrous THF was added 4-methylmorpholine (35mg, 0.34mmol) and isobutyl carbonochloridate (49mg, 0.36mmol) under nitrogen atmosphere at-10. The reaction mixture was stirred for 30minat-10, then pyrimidin-5-amine (32mg, 0.34mmol) was added. After reacting for another 30minat-10, the reaction mixture was warmed to room temperature and stirred for 6h. The solvent was evaporated and the residues was dissolved in ethyl acetate (10mL), washed with water (10mL¡Á3) and brine (10mL¡Á3). The organic layer was dried over Na2SO4, concentrated under vacuum and purified on silica gel to afford the compound 18g as a white solid (56mg, 43%). Mp: 150.0-153.0C. HPLC purity=99.33%, HPLC tR=15.10min (Method B). The 1H NMR showed 12:1 ratio of atropisomers. 1H NMR (500MHz, CDCl3) delta 9.34 (s, 1H), 8.89 (s, 1H), 8.81 (s, 2H), 7.07 (d, J=8.5Hz, 2H, [6.97 minor isomer]), 6.83 (d, J=8.5Hz, 2H, [6.70 minor isomer]), 4.78 (s, 2H, [4.67 minor isomer]), 4.30-4.21 (m, 1H), 4.02 (s, 2H, [4.16 minor isomer]), 2.49 (t, J=7.5Hz,2H), 1.62-1.51 (m, 2H), 1.27 (d, J=6.5Hz, 6H, [1.16 minor isomer]), 0.89 (t, J=7.5Hz, 3H). 13C NMR (125MHz, CDCl3) delta 168.86, 167.39, 154.63, 152.97, 146.63, 135.37, 132.46, 128.59, 113.26, 66.17, 48.37, 45.19, 36.05, 23.59, 19.95, 12.73. HRMS (ESI) m/z: calcd for C20H27N4O3 [M+ H]+, 371.2078; found 371.2088.

20744-39-2, The synthetic route of 20744-39-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Yu, Jianjun; Xu, Lei; Hong, Duidui; Zhang, Xiaotuan; Liu, Jieyu; Li, Daqiang; Li, Jia; Zhou, Yubo; Liu, Tao; European Journal of Medicinal Chemistry; vol. 161; (2019); p. 543 – 558;,
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