Heterocyclic Building Blocks-Pyridazine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.51149-08-7,3,6-Dichloropyridazine-4-carboxylic acid,as a common compound, the synthetic route is as follows.

51149-08-7, Example 5( 6-Chloro-1 H -indol-3-yl)[ 6-chloro-[3-( 4-.fluorobenzyl)amino ]pyridazin-4-yl]methanone 3,6-Dichloropyridazine-4-carbonyl chloride. 3,6-Dichloropyridazine-4-carboxylic acid (Aldrich; 1.13 g, 5.86 mmol) in toluene (20 mL) containing 2 drops of DMF was treated with neat SOCI2 (4 mL). The mixture heated to reflux for 3h and then allowed to cool. The resulting red-orange mixture was decanted and cone, in vacuo. The residue was redis solved in toluene and cone to give 1.22 g of the product.

51149-08-7 3,6-Dichloropyridazine-4-carboxylic acid 433804, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; HOGENKAMP, Derk; WO2013/169907; (2013); A1;,
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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.

Preparation 9.1: 5-(4-methylpiperazin-l-yl)pyridazin-4-amine 7o Step 1: 3,4-dichloro-5-(4-methylpiperazin-l-yl)pyridazine [00283] 3,4,5-Trichloropyridazine (3 g, 16.36 mmol) was dissolved in dry NMP (18 mL) and cooled in an ice-bath. DIPEA (2.326 g, 3.135 mL, 18 mmol) was added, followed, dropwise, by 1-methylpiperazine (1.721 g, 1.906 mL, 17.18 mmol). The resulting mixture was stirred at RT overnight. The reaction mixture was concentrated under reduced pressure to give an brown solid whichwas partitioned between 10% MeOH in DCM and saturated NaHC03. The aqueous layer was extracted with further 10% MeOH in DCM (5x20mL) and the combined organics were dried over Na2S04, filtered and concentrated under reduced pressure to give a brown oil which was purified by column chromatography (7.5% MeOH in DCM, ~300mL silica, loaded in DCM) to provide 3,4-dichloro-5-(4-methylpiperazin-l- yl)pyridazine as a light yellow solid (2.36g, 58% Yield)., 14161-11-6

The synthetic route of 14161-11-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; VERTEX PHARMACEUTICALS INCORPORATED; BRENCHLEY, Guy; CHARRIER, Jean-damien; DAVIS, Chris; DURRANT, Steven; JARDI, Gorka, Etxebarria I; FRAYSSE, Damien; JIMENEZ, Juan-miguel; KAY, David; KNEGTEL, Ronald; PIERARD, Francoise; PINDER, Joanne; SHAW, David; STORCK, Pierre-henri; STUDLEY, John; TWIN, Heather; WO2014/143241; (2014); A1;,
Pyridazine – Wikipedia
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20744-39-2, Pyridazin-4-amine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 292-{[(4-Fluorophenyl)methyl]oxy}-4-(1 -methyl-1 H-pyrazol-4-yl)-5-(4- morpholinylcarbonyl)-/V-4-pyridazinylbenzamide (E29) To a solution of (4-fluorophenyl)methyl 2-{[(4-fluorophenyl)methyl]oxy}-4-(1-methyl-1 H- pyrazol-4-yl)-5-(4-morpholinylcarbonyl)benzoate (may be prepared as described inDescription 32; 191 mg, 0.35 mmol) in tetrahydrofuran (6 ml) was added lithium hydroxide (60 mg, 2.51 mmol) and water (1.5 ml). The mixture was stirred for 3 hours then quenched with 2M hydrochloric acid (1.26 ml, 2.51 mmol). The solvent was removed in vacuo and the residue was redissolved in N,N-dimethylformamide (6 ml) and diisopropylethylamine (0.12 ml, 0.70 mmol), 4-pyridazinamine (39.8 mg, 0.42 mmol), 1-hydroxy-7-azabenzotriazole (57.0 mg, 0.42 mmol) and EDC (100 mg, 0.52 mmol) were added. The reaction was stirred for 18 hours then the solvent was removed in vacuo and the residue purified by MDAP to yield the title compound as a white solid. 64 mg.MS (electrospray): m/z, [M+H]+ = 5171 H NMR (400 MHz, DMSO-d6); 2.74 – 3.13 (3 H, m), 3.35 – 3.75 (5 H, m), 3.86 – 3.96 (3 H, m), 5.33 (2 H, s), 7.15 – 7.29 (2 H, m), 7.43 (1 H, s), 7.50 – 7.66 (3 H, m), 7.74 (1 H, s), 7.94 – 8.07 (2 H, m), 8.95 – 9.10 (1 H, m), 9.20 (1 H, d, J=1.76 Hz), 10.69 (1 H, s)., 20744-39-2

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

Reference£º
Patent; GLAXO GROUP LIMITED; ANDREOTTI, Daniele; DAI, Xuedong; EATHERTON, Andrew John; JANDU, Karamjit Singh; LIU, Qian; PHILPS, Oliver James; WO2012/28629; (2012); A1;,
Pyridazine – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.35857-89-7,6-Chloropyridazine-3-carbonitrile,as a common compound, the synthetic route is as follows.

To a solution of 2H-tetrazole (1.83 1 g, 26.1 mmol) in DMF (30 ml) was added Cs2CO3(8.52 g, 26.1 mmol) at 0 C. The resulting solution was stirred at 0 C for 15 mm followed byaddition of 6-chloropyridazine-3-carbonitrile (Liu, et al., I Med. Chem. 2007, 50, 3086-3 100) (3.04 g, 21.79 mmol). The resulting solution was stirred at rt for 30 mm, then heated at 90 C for 30mm. The mixture was cooled to rt, and partitioned between EtOAc and sat. NaHCO3. The organic layer was washed with sat.NaHCO3 three times, dried over Na2504, and concentrated.The residue was stirred with DCM. The solid was collectted by filtration to give the title compound., 35857-89-7

As the paragraph descriping shows that 35857-89-7 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; BISWAS, Dipshikha; DING, Fa-Xiang; DONG, Shuzhi; GU, Xin; JIANG, Jinlong; PASTERNAK, Alexander; SUZUKI, Takao; VACCA, Joseph; XU, Shouning; WO2015/103756; (2015); 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.19064-65-4,3-Methoxypyridazine,as a common compound, the synthetic route is as follows.

Step 1: A mixture of 3-methoxypyridazine (12.0 mL, 130 mmol) and oxirane-2,2,3,3- tetracarbonitrile (20 g, 140 mmol) in THF (240 mL) was stirred at 0 oC for 2 h and at 4 oC for 40 h. The reaction was concentrated to afford crude dicyano(3-methoxypyridazin-1-ium-1- yl)methanide as a solid, which was taken to the next step without further purification. 1H NMR (DMSO-d6, 400 MHz): delta 8.56 (d, J = 6.0 Hz, 1H), 7.94 (m, 1H), 7.14 (d, J = 9.2 Hz, 1H), 3.97 (s, 3H)., 19064-65-4

19064-65-4 3-Methoxypyridazine 292493, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; LIM, Jongwon; ALTMAN, Michael, D.; BRUBAKER, Jason, D.; GIBEAU, Craig, R.; (94 pag.)WO2016/144847; (2016); A1;,
Pyridazine – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7252-84-8,3-Amino-6-methoxypyridazine,as a common compound, the synthetic route is as follows.

Example 62: Preparation of 2-{3-[2-(4-chlorophenyl)ethyl]-5-oxo-l-phenyl-2- sulfanylideneimidazolidin-4-yl}-N-(6-methoxypyridazin-3-yl)acetamide. TBTU (253.3 mg; 0.77 mmol; 1.5 eq) and DIPEA (179 mu 1-03 mmol; 2 eq) were added to a solution of 2-{3-[2-(4-chlorophenyl)ethyl]-5-oxo-l-phenyl-2- sulfanylideneimidazolidin-4-yl} acetic acid (1-3) (200 mg; 0.51 mmol; 1 eq) in dioxane (5 mL). After 20 minutes, 6-methoxypyridazin-3-amine (128.9 mg; 1.03 mmol; 2 eq) in dimethylformamide (0.1 mL) was added. The reaction mixture was stirred at room temperature over the week-end. After concentration to dryness, saturated ammonium chloride (30 mL) was added and the aqueous layer was extracted with ethyl acetate (3 x 30 mL). The combined organic layers were washed with saturated sodium chloride (3 x 30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude was precipitated in methanol. The title compound, the title compound 2-{3-[2-(4-chlorophenyl)ethyl]-5-oxo-l-phenyl- 2-sulfanylideneimidazolidin-4-yl } -N-(6-methoxypyridazin-3-yl)acetamide was obtained in 22% yield (55.8 mg) as a grey-white powder. 1H-NMR (CDC13): delta (ppm) 2.9 (m, 1H), 3.03 (m, 1H), 3.22 (m, 1H), 3.45 (m, 1H), 3.74 (m, 1H), 3.98 (s, 3H), 4.17 (m, 1H), 4.8 (t, 1H, J = 4.2 Hz), 7.38 (m, 10H), 8.17 (m, 1H), 11.19 (s, 1H); MS (ESI+): m/z = 495.9, 497.8 [M+H]+ ., 7252-84-8

As the paragraph descriping shows that 7252-84-8 is playing an increasingly important role.

Reference£º
Patent; VIVALIS; GUEDAT, Philippe; BERECIBAR, Amaya; CIAPETTI, Paola; VENKATA PITHANI, Subhash; TROUCHE, Nathalie; WO2013/171281; (2013); 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.15456-86-7,4-Bromo-1,2-dihydropyridazine-3,6-dione,as a common compound, the synthetic route is as follows.

The solid, divided into two batches, was treated with phosphorus oxychloride (2×200 ml) and heated to reflux for 3.5 h. The mixture was cooled, evaporated and azeotroped with toluene. The residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution and extracted with DCM twice more. The organic extracts were dried and evaporated. This residue was re-dissolved in dichloromethane, and chromatographed on silica gel (300 g) (DCM as eluent) to give a white solid (101.5 g, 87%). (LC/MS analysis showed ca. 20-30% impurity, isomers of bromo-dichloropyridazine)., 15456-86-7

The synthetic route of 15456-86-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2008/6648; (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.63001-30-9,Methyl 6-oxo-1,6-dihydropyridazine-3-carboxylate,as a common compound, the synthetic route is as follows.

63001-30-9, To a solution of methyl 6-oxo-1 ,6-dihydropyridazine-3-carboxylate (1 .1 g, 7.14 mmol) in A/,A/-dimethylformamide (20 ml_) at room temperature was added potassium carbonate (1 .97 g, 14.3 mmol) and iodoethane (2.23 g, 14.3 mmol). The reaction mixture was stirred at 70 C for 16 h, cooled to room temperature, diluted with water (300 ml_) and extracted with ethyl acetate (80 ml_ c 3). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to afford methyl 1 -ethyl-6-oxo-1 ,6-dihydropyridazine-3-carboxylate (1 .0 g, 5.49 mmol, 76.9%) as a white solid. LCMS (ESI) m/z: 183.1 [M+H]+.

The synthetic route of 63001-30-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; YUMANITY THERAPEUTICS, INC.; LE BOURDONNEC, Bertrand; LUCAS, Matthew; OZBOYA, Kerem; PANDYA, Bhaumik; TARDIFF, Daniel; TIVITMAHAISOON, Parcharee; WRONA, Iwona; (475 pag.)WO2019/183587; (2019); 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.38956-79-5,3-Hydrazinyl-6-methylpyridazine,as a common compound, the synthetic route is as follows.

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

38956-79-5 3-Hydrazinyl-6-methylpyridazine 12379804, apyridazine compound, is more and more widely used in various fields.

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;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6082-66-2,3,4,6-Trichloropyridazine,as a common compound, the synthetic route is as follows.,6082-66-2

3,4,6-Trichloropyridazine (2 g) and diethylamine (2.4 ml) were initially charged in toluene (10 ml) and left to stand at RT for 3 days. Then the mixture was admixed with water and EA, and the EA phase was removed. The EA phase was washed three times with water, dried over magnesium sulfate, filtered and concentrated. The residue was purified using silica gel (70 g cartridge, n-heptane/EA gradient 0-50% within 60 min). 1.1 g of the title compound were obtained.LC-MS rt: 1.24 min [M+H]+: 248.1 (met. a)

6082-66-2 3,4,6-Trichloropyridazine 95123, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; sanofi-aventis; US2011/34451; (2011); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem