Heterocyclic Building Blocks-Pyridazine

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-lH-pyridazine-3-carboxylate (2.59 g, 1.0 eq, 16.64 mmol, from Combi-Blocks) and potassium acetate, KOAc (6.60 g, 4.0 eq) in 50 mL of acetic acid, glacial, cooled at 0 C, bromine, Br2 (2.54 mL, 2.96 eq), is added. After the addition the mixture is stirred at 80 C for 5 h. The mixture is poured on 200 mL of saturated Na2S203 water solution. The mixture is extracted with EtOAc (10 % THF, 3 times, 150 mL in total). The gathered organic layers are washed with 200 mL of 0.01 N HC1 water solution and 200 mL of brine and dried over Na2S04. After filtration the solvent is evaporated and the resulting crude is purified by flash column chromatography (Si02, DCM / EtOAc 95:5 to 0: 100) to afford the desired compound. LCMS: MW (calcd): 233; m/z MW (obsd): 235 (M+H).

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

Reference£º
Patent; GALAPAGOS NV; MAMMOLITI, Oscar; JANSEN, Koen, Karel; PALISSE, Adeline, Marie, Elise; JOANNESSE, Caroline, Martine, Andree-Marie; MENET, Christel, Jeanne, Marie; ALLART, Brigitte; EL BKASSINY, Sandy; (186 pag.)WO2017/148787; (2017); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.65202-50-8,Methyl 6-chloropyridazine-3-carboxylate,as a common compound, the synthetic route is as follows.

65202-50-8, Methyl 6-{3-r(2-bromophenyl)oxylazetidin-l-yl}pyridazine-3-carboxylate; Into a flame-dried 100 mL round-bottom flask equipped with a magnetic stirring bar and under N2 was added methyl 6-chloropyridazine-3-carboxylate (848 mg, 4.91 mmol), 3- [(2-bromophenyl)oxy]azetidine hydrochloride (1.3 g, 4.91 mmol) and potassium carbonate (2.04 g, 14.7 mmol) in dioxane (30 mL). The reaction mixture was heated to reflux for 16 h overnight. The reaction mixture was cooled to room temperature and quenched with water (10 mL). The reaction mixture was concentrated and a beige solid precipitated out of solution. The solid was diluted with water (20 mL) and filtered through WhatmanNo.l paper on a Hirsch funnel, washing with water. The resulting beige solid was dried on the vacuum pump overnight, giving the desired product.MS (ESI, Q+) m/z 364 (M + 1, 79Br), 366 (M + 1, 81Br).

65202-50-8 Methyl 6-chloropyridazine-3-carboxylate 12379801, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK FROSST CANADA LTD.; WO2007/143823; (2007); A1;,
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84956-71-8, 2-(tert-Butyl)-4,5-dichloropyridazin-3(2H)-one is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

84956-71-8, Example 3 Synthesis of 2-tert-butyl-4-chloro-5-[2-(2-methyl-4-n-pentylphenoxy)ethylthio]-3(2H)-pyridazinone (Compound No. 12) In 20 ml of methanol were dissolved 1.8 g of 2-tert-butyl-4,5-dichloro-3(2H)-pyridazinone and 1.9 g of 2-(2-methyl-4-n-pentylphenoxy)ethylmercaptan, and then to the mixture was added dropwise a solution of 0.5 g of sodium methoxide dissolved in 5 ml of methanol. After dropwise addition, the mixture was stirred at room temperature for 1 hour to complete the reaction. Then, methanol was distilled off under reduced pressure, and an oily product which was separated by adding water was extracted with ethyl acetate The extract was washed with water, dried over anhydrous sodium sulfate, and then ethyl acetate was distilled off under reduced pressure. The oily product obtained was isolated by column chromatography (Wako Gel C-200, eluted with toluene: ethyl acetate = 9: 1) to give 2.8 g of the title compound as colorless oily liquid.

The synthetic route of 84956-71-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UBE INDUSTRIES, LTD.; RIKAGAKU KENKYUSHO; EP283271; (1990); A3;,
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88497-27-2, 3-Amino-6-bromopyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6-bromo-3-pyridazinamine (77mg, 0.44mmol), (E)-N?-(2-cyano-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-N,N-dimethylformamidine (120mg, 0.40mmol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex(32mg, 0.04mmol) and cesium carbonate (391mg, 1.2mmol) were dissolved in N,N-dimethylformamide (8mL) andwater (0.8mL), the mixture was stirred at 85C under argon atmosphere for 4 hours, then filtered and concentrated togive a residue which was purified by column chromatography to give 90mg yellow solid with a yield of 84%.

88497-27-2, 88497-27-2 3-Amino-6-bromopyridazine 2794779, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; Shanghai Pharmaceuticals Holding Co., Ltd.; XIA, Guangxin; LI, Di; ZUO, Hongjian; WU, Guangsheng; DUAN, Lingjun; ZHANG, Jing; MAO, Yu; LIU, Yanjun; (152 pag.)EP3424928; (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.50681-25-9,4-Pyridazinecarboxylic Acid,as a common compound, the synthetic route is as follows.

50681-25-9, General procedure: 1,1?-carbonyldiimidazole (1.23 g, 7.57 mmol) was added to a suspension of pyrimidine-5-carboxylic acid (783 mg, 6.31 mmol) in DCM (20 mL) and the mixture was stirred at room temperature for 15 min before addition of N,O-dimethylhydroxylamine hydrochloride (739 mg, 7.57 mmol). The mixture was stirred at room temperature for 5 d, then was diluted with saturated aqueous NH4Cl and water and extracted with DCM. The organic phase was washed with water, and the aqueous phases were back-extracted with DCM. The organic phase was dried (Na2SO4), filtered, and concentrated, affording the crude title compound as a light yellow oil which was used without further purification in the next reaction . The title compound was prepared using pyridazine-4-carboxylic acid in place of pyrimidine-5-carboxylic acid using the procedure described for Intermediate 28, step a, except that the reaction was run for 2 days and the crude product was purified by flash column chromatography (silica gel, gradient 0-3% MeOH-DCM).

As the paragraph descriping shows that 50681-25-9 is playing an increasingly important role.

Reference£º
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); 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

6082-66-2, A MW vial was charged with 3,4,6-trichloropyridazine (5 g, 27.3 mmol) and 7N NH3 in MeOH (19.47 mL, 136 mmol). The MW vial was sealed and the resulting mixture was submitted to MWirradiation at 100 00 for 30 mm. The reaction was cooled down to RT and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (hexane/EtOAc 35-60%) to afford the title product (1.49 g, 8.63 mmol, 32% yield) as yellow solid. tR: 1.61 mm (HPLC 1); tR: 0.45 mm (LC-MS 2); ESI-MS: 163 [M+H] (LC-MS 2); R = 0.40 (hexane/EtOAc 1:1).

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

Reference£º
Patent; NOVARTIS AG; BLANK, Jutta; BORDAS, Vincent; COTESTA, Simona; GUAGNANO, Vito; RUEEGER, Heinrich; VAUPEL, Andrea; WO2014/191896; (2014); 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.65202-50-8,Methyl 6-chloropyridazine-3-carboxylate,as a common compound, the synthetic route is as follows.,65202-50-8

A solution of THF (2.5 mL) and toluene (10 mL), and methylmagnesiurn chloride (3.0 M, 9.7 mL) were stirred at -2O0C under N2 atmosphere followed by the addition of f-BuOH (0.5 mL, 5.79 mrnol) in THF (7 mL) dropwise. The solution was allowed to stir for 30 min and warmed to 30C and cooled backed down to -200C followed by the addition of the methyl 6- chloropyridazine-3-carboxylate (1.0 g, 5.79 mmol) in portions. The solution quickly turned dark violet and was stirred at 00C for 30 min. The solution was then poured into a flask containing 1 N aqueous hydrochloric acid at -50C, diluted with ethyl acetate, and stirred for 10 min. The layers were then separated and the organic layer was washed with saturated aqueous sodium bicarbonate and brine. The acidic aqueous layer was neutralized with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layers were combined and concentrated in vacuo. Purification via flash chromatography (silica, 0-100percent ethyl acetate/hexanes) provided the title compound. LRMS (ESI) calc’d for C7H10ClN2O [M+H]+: 173.1, Found: 173.1

As the paragraph descriping shows that 65202-50-8 is playing an increasingly important role.

Reference£º
Patent; MERCK & CO., INC.; MACHACEK, Michelle, R.; HAIDLE, Andrew; ZABIEREK, Anna, A.; KONRAD, Kaleen, M.; ALTMAN, Michael, D.; WO2010/11375; (2010); 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.20074-67-3,Perchloropyridazine,as a common compound, the synthetic route is as follows.,20074-67-3

1.69 g (10.10 mmol) of carbazole was added to a 250 ml three-necked flask, Then, 100 mL of N,N-dimethylformamide was added as a reaction solvent, Stirred for 10 min on a magnetic stirrer. Under ice-cooling, 0.49 g (20.19 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h. 0.50 g (2.30 mmol) of 3,4,5,6-tetrachloropyridazine was dissolved in 20 ml of N,N-dimethylformamide was added dropwise to the reaction system. After completion of the addition, the reaction was carried out at 60 C for 15 hours under nitrogen atmosphere. After the reaction, The reaction solution was poured into 150 ml of dilute hydrochloric acid at a concentration of 10% Decompression pumping, washing, drying, The crude product was treated with petroleum ether and ethyl acetate (PE:EA=10:1) The mobile phase was subjected to column chromatography to remove impurities, and then pure methylene chloride (DCM) The column was evaporated to give 1.16 g of a pale yellow solid in 68.0% yield.

As the paragraph descriping shows that 20074-67-3 is playing an increasingly important role.

Reference£º
Patent; Dalian University of Technology; LI, JIUYAN; SUI, KAI; LIU, DI; (19 pag.)CN106243091; (2016); A;,
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Pyridazine | C4H4N2 – PubChem

19064-64-3, 3,6-Dichloro-4-methylpyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 3,6-dichloro-4-methylpyridazine (5 g, 30.7 mmol) and concentrated NH40H solution (100 ml) was heated to 120 in a sealed autoclave for 18 hrs at 6 bar. The mixture was cooled to r.t, diluted with water (200 ml) and stirred in an ice bath for 2 hrs. The solid was collected by filtration, washed with water and dried. The filtrate was extracted with CH2Cl2/MeOH (9: 1). The organic was washed with brine, dried over MgSC^, filtered and evaporated. The precipitate from the reaction mixture and the solid isolated by extraction were combined. This crude product was purified by column chromatography using a CH2Cl2/MeOH gradient as eluent, to provide 6-chloro-4-methylpyridazin-3-amine (456 mg, 10%) and 6-chloro-5-methylpyridazin- 3-amine (350 mg, 8%>), both as off-white solids. MS: M = 144.1 (M+H)+ (both isomers)

19064-64-3, 19064-64-3 3,6-Dichloro-4-methylpyridazine 87923, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; LERNER, Christian; WO2014/72261; (2014); 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.135034-10-5,3-Chloro-6-iodopyridazine,as a common compound, the synthetic route is as follows.

To a stirred solution of Intermediate 2 (0.25 g, 0.8 mmol) in dry DMF (5 mL), TEA (0.36 ml,2.85 mmol) and 3-chloro-6-iodopyridazine (0.123 g, 0.99 mmol) were added at rt and the reaction mixture was stirred at 90 C overnight. The resulting reaction mixture was cooled to rt and DMF was evaporated under reduced pressure. To the resulting crude mixture, water (20 mL) was added and the product was extracted with EtOAc (2 x 30 mL). Theresulting organic layer was dried over Na2SO4 and concentrated. This crude product waspurified by flash column chromatography to afford the title compound ( off white solid). 1HNMR (400 MHz, CDCI3): 68.86-8.84 (m, 2H), 8.11 (d, J = 8.8 Hz, IH), 8.03 (d, J = 2.0 Hz,I H), 7.90 (dd, J = 8.8, 2.0 Hz, I H), 7.45 (d, J = 9.6 Hz, I H), 6.60 (d, J = 9.6 Hz, I H), 3.65-3.58 (m, 5H), 2.73-2.67 (m, 2H), 2.59-2.54 (m, 2H), 1.51 (d, J = 6.8 Hz, 3H). LCMS:(Method A) 447.0 (M +H), Rt. 2.13 mm, 99.59% (Max). HPLC: (Method A) Rt. 2.16 mm,98.99% (Max).

135034-10-5, As the paragraph descriping shows that 135034-10-5 is playing an increasingly important role.

Reference£º
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut, Gajendra; (280 pag.)WO2017/144633; (2017); A1;,
Pyridazine – Wikipedia
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