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Facile synthesis of 4,5-disubstituted-3(2H)-pyridazinones

4,5-Disubstituted-3(2H)-pyridazinones were initially synthesized via sodium alkoxide additions to an advanced bromide intermediate. A small parallel chemistry effort resulted in a poor success rate, and we thus increased the reactivity of the reaction partner by performing a copper-catalyzed Finkelstein reaction. Copper-catalyzed coupling of a diverse set of alcohols with the resulting iodide resulted in a more successful effort. A number of alternative syntheses of this series of compounds are also described and these methods proved to be versatile, efficient, and amenable to parallel synthesis.

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Pyridazine – Wikipedia,
Pyridazine | C4H4N3172 – PubChem

 

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Note that a catalyst decreases the activation energy for both the forward and the reverse reactions and hence accelerates both the forward and the reverse reactions.5788-58-9, you can also check out more blogs about5788-58-9

5788-58-9, In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 5788-58-9, name is 4,5-Dibromopyridazin-3(2H)-one, introducing its new discovery.

PYRIDAZINONYL MACROCYCLIC HEPATITIS C SERINE PROTEASE INHIBITORS

The present invention relates to compounds of Formula I, or pharmaceutically acceptable salts, esters, or prodrugs thereof, which inhibit serine protease activity, particularly the activity of hepatitis C virus (HCV) NS3-NS4A protease. Consequently, the compounds of the present invention interfere with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a subject by administering a pharmaceutical composition comprising a compound of the present invention.

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Pyridazine – Wikipedia,
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Studies on improved synthesis of 2?-deoxyribonucleosides of pyridazine derivatives

A number of 2?-deoxyribonucleosides of halogenated pyridazine derivatives were prepared by glycosylation of their respective potassium or DBU salts in acetone. The reaction yielded predominatly beta-anomers that could be purified by simple crystallization or column chromatography. Of the studied pyridazines and deoxynucleosides, only 4-bromo-6-chloro-pyridazin-3-one and 6-chloro-2-(2?-deoxyribofuranosyl)pyridazin-3-one showed modest inhibition of CK2 kinase.

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Pyridazine – Wikipedia,
Pyridazine | C4H4N3173 – PubChem

 

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5788-58-9,5788-58-9, 4,5-Dibromopyridazin-3(2H)-one is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4,5-dibromo-pyridazin-3-one (2.00 g, 7.88 mmol) was dissolved N, N-dimethylformamide (10 mL), potassium carbonate (1.31 g, 9.46 mmol), iodomethane (736 muL, 11.8 mmol) and the mixture was stirred for 2 hours at 50 . The reaction mixture was concentrated under reduced pressure, the residue was diluted with water, and extracted with ethyl acetate. The organic phase was dried anhydrous sodium sulfate and concentrated under reduced pressure, the resulting residue was dissolved in ethyl acetate / methanol was added to give the title compound precipitated solid by filtered and dried (755 mg). Further, to give the title compound (1.20 g) by purifying the residue and the filtrate was concentrated under reduced pressure, and the resulting by silica gel column chromatography.

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Reference£º
Patent; AJINOMOTO COMPANY INCORPORATED; UENO, HIROKAZU; HAYAKAWA, NOBUHIKO; YOKOYAMA, RYOHEI; IWASAKI, KANA; YAMAMOTO, TAKASHI; (67 pag.)JP2016/37467; (2016); A;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

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General procedure: To a solution of 4,5-dichloro-2,3-dihydropyridazin-3-one (65.6 mg, 0.40 mmol, 1 equiv.) in DMA(2 mL) were added 1-[(2,4-difluorophenyl)methyl]piperazin-2-one (90 mg, 0.40 mmol, 1 equiv.) and DIEA(102.8 mg, 0.80 mmol, 2 equiv.) at room temperation. The resulting mixture was stirred for 16 h at 100 degrees C. The reaction was monitored by LCMS. The product was purified by reverse phase flash with the following conditions (Column: spherical C18, 20-40 um,120g; Mobile Phase A: Water(5mmol/L NH4HCO3), Mobile Phase B: MeCN; Flow rate:45mL/min; Gradient: 20% B to 40% B in 25min; 220 nm) to afford 4-chloro-5-[4-[(2,4- difluorophenyl)methyl]-3-oxopiperazin-1-yl]-2,3-dihydropyridazin-3-one (28.6 mg, 20.27%) as a yellow solid

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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;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

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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 tert-butyl (3R)-3-methylpiperazine-1-carboxylate(500 mg, 2.50 mmol, 1 equiv.) and DIEA(645.3 mg, 4.99 mmol, 2 equiv.) in DMF(5 mL) was added 4,5- dibromo-2,3-dihydropyridazin-3-one (760.6 mg, 3.00 mmol, 1.2 equiv.) in portions at 100 degrees C overnight. The residue product was purified by reverse phase flash with the following conditions: MeCN/H2O(35%-75%,45min) to afford tert-butyl (3R)-4-(5-bromo-6-oxo-1,6- dihydropyridazin-4-yl)-3-methylpiperazine-1-carboxylate(150mg,16.10%) as a yellow oil

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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;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

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5788-58-9, EXAMPLE 1 4-bromo-5-(3-n-propoxy-4-methoxy-N-methylbenzylamino)-3(2H)pyridazinone (Compound No. 6) STR28 A mixture comprising 300 mg of 4,5-dibromo-3(2H)pyridazinone, 740 mg of 3-n-propoxy-4-methoxy-N-methylbenzylamine and 10 ml of ethanol, was refluxed under stirring for 7 hours. Then, ethanol was distilled off under reduced pressure, dilute hydrochloric acid was added to the residue thereby obtained, and the mixture was extracted with ethyl acetate. The extract was washed twice with water and dried over sodium sulfate. Then, the solvent was distilled off to obtain a yellow solid substance. The product was crystallized from ethyl acetate, to obtain 310 mg of the above identified compound having a melting point of from 149 to 150 C. as light yellow crystals. NMR delta: 7.53(1H, s), 6.75(3H, s), 4.53(2H, s), 3.91(2H, t), 3.81(3H, s), 3.01(3H, s), 1.84(2H, hexalet), 1.01(3H, t). MS (m/e): 302(M+ -Br,100%), 179, 137.

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Reference£º
Patent; Nissan Chemical Industries Ltd.; US4978665; (1990); A;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

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5788-58-9, A mixture of 25 g (0.1 mol) of 4,5-dibromo-3 (2H) -pyridazinone, 93 g (0.5 mol) of tributylamine,(HFC-23) at room temperature, and the mixture was stirred at 80 C, and the reaction was carried out. After the reaction was followed by thin layer chromatography, the reaction mixture was cooled with 10 ml of methylene chloride And purified by column chromatography (the stationary phase was silica gel GF254, eluent ethyl acetate / petroleum ether V / V = 1: 1) to give 17.2 g of a white solid product as a white powder,Yield 90%.

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Reference£º
Patent; Pei, Qing; (6 pag.)CN106083731; (2016); A;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

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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 (3S)-3-methyl-1-[(2-methylphenyl)methyl]piperazine (500 mg, 2.45 mmol, 1 equiv.) and DIEA(632.6 mg, 4.89 mmol, 2 equiv.) in DMA(5 mL) was added 4,5- dibromo-2,3-dihydropyridazin-3-one (745.6 mg, 2.94 mmol, 1.2 equiv.) in portions at 100 degrees C overnight

The synthetic route of 5788-58-9 has been constantly updated, and we look forward to future research findings.

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;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

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The synthetic route of 5788-58-9 has been constantly updated, and we look forward to future research findings.

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, EXAMPLE 6 4-Bromo-5-(3-n-pentyloxy-4-methoxybenzylamino)-3(2H)-pyridazinone (Compound No. 39) STR26 A mixture comprising 1.52 g of 4,5-dibromo-3(2H) pyridazinone, 4.01 g of 3-n-pentyloxy-4-methoxybenzylamine and 60 ml of ethanol was refluxed under stirring for 7.5 hours. Then, ethanol was distilled off under reduced pressure, and the residue thus obtained was extracted with ethyl acetate. The extract was sequentially washed with dilute hydrochloric acid and water, and dried over sodium sulfate. Then, the solvent was distilled off, and the residue thus obtained was crystallized from ethyl acetate-diethyl ether to obtain 1.42 g of the above identified compound as pale yellow crystals having a melting point of from 148 to 150 C. NMR(CDCl3)delta: 7.51 (1H, s), 6.82 (3H, s), 5.28 (1H, brs), 4.51, 4.41 (total 2H, each s), 3.97 (2H, t), 3.84 (3H, s), 2.05-1.05 (6H, m), 0.96 (3H, t) Mass (m/e): 395 (M+), 316 (100%), 207, 137

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Reference£º
Patent; Nissan Chemical Industries Ltd.; US4892947; (1990); A;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem