Heterocyclic Building Blocks-Pyridazine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.54709-94-3,5-Methylpyridazin-3(2H)-one,as a common compound, the synthetic route is as follows.,54709-94-3

6-Oxo-l,6-dihydro-pyridazine-4-carboxylic acidThe title compound from Example 18.2 (0.90 g, 8.17 mmol) was stirred in concentrated sulfuric acid (13 mL) and heated to 45 0C. Potassium permanganate (3.6 g, 12.25 mmol) was added portion wise over 30 min to avoid letting the temperature rise. The reaction was allowed to stir for a further 30 min at 45 0C. The reaction was then cooled to r.t. and ice was added to the reaction mixture. The resulting precipitate was collected by vacuum filtration, washing with cold water and diethyl ether to give 0.978 g (87%) of the title compound as the a pale green solid. 1H NMR (300 MHz, CDCl3) delta 13.39 (br, IH), 8.12 (s, IH), 7.22 (s, IH).

54709-94-3 5-Methylpyridazin-3(2H)-one 327041, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; ASTRAZENECA AB; ISAAC, Methvin; SLASSI, Abdelmalik; EDWARDS, Louise; DOVE, Peter; XIN, Tao; STEFANAC, Tomislav; WO2008/41075; (2008); A1;,
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51149-08-7,51149-08-7, 3,6-Dichloropyridazine-4-carboxylic acid is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of a portion (10 g) of the material so obtained, concentrated sulphuric acid(10 drops) and anhydrous ethanol (50 ml) was heated to reflux for 24 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and water. The organic phasewas dried over magnesium sulphate and evaporated. The residue was dissolved in phosphorylchloride (70 ml) and the solution was heated to 70C for 2 hours. The resultant mixture wascooled to ambient temperature, poured onto a mixture of ice and water and extracted with ethylacetate. The organic layer was washed with a saturated aqueous sodium bicarbonate soluiton,dried over magnesium sulphate and evaporated. The residue was purified by columnchromatography on silica using a 4:1 mixture of petroleum ether (b.p 40-60C) and ethylacetate as eluent. There was thus obtained ethyl 3,6-dichloropyridazine-4-carboxylate as an oil (5.7 g); NMR Spectrum: (CDC13) 1.45 (t, 3H), 4.49 (q, 2H), 7.87 (s,1H); Mass Spectrum: M+H4 221.

As the paragraph descriping shows that 51149-08-7 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/108707; (2004); 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 (100 mg, 0.483 mmol) and 6- (methylthio) pyridin-3-amine (101 mg, 0.724 mmol) were dissolved in ethanol (2 mL), It was heated to 110 C in a microwave reactor and stirred for 1 hour.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 = 2/1 to 1/1),The target product 6-chloro-4-((6- (methylthio) pyridin-3-yl) amino) pyridazine-3-carboxylic acid methyl ester 13a (100 mg, yellow solid) was obtained,Yield: 66%.

372118-01-9, As the paragraph descriping shows that 372118-01-9 is playing an increasingly important role.

Reference£º
Patent; Beijing Nuochengjianhua Pharmaceutical Technology Co., Ltd.; Chen Xiangyang; Pang Yucheng; (142 pag.)CN110818641; (2020); A;,
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19064-67-6, 6-Chloro-3-hydroxypyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 256 6-chloro-2-(pyridine-3-ylmethyl)-2H-pyridazine-3-one 6-chloro-2H-pyridazine-3-one (1.00 g) was dissolved in DMF (76 mL). To this solution, 60% sodium hydride (370 mg) was added at room temperature in an argon atmosphere and the mixture was vigorously stirred at 50 C. Meanwhile, 60% sodium hydride (370 mg) was added to a solution of 3-(chloromethyl)pyridine hydrochloride (1.51 g) in DMF at -40 C. in an argon atmosphere and the solution was allowed to warm to room temperature. Using a cannula, this solution was poured into the pyridazinone solution and the mixture was stirred first at 50 C. for 90 min and then at room temperature for 18 hours. Subsequently, a saturated ammonium chloride solution was added and the solvent was concentrated. Water was then added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent and subsequent purification by silica gel column chromatography (ethyl acetate: petroleum ether=7:3, followed by methanol:ethyl acetate=5:95) afforded the title compound as a colorless powder (1.30 g). 1H NMR (200 MHz, CDCl3) delta 8.70 (1H, d, J=1.5 Hz), 8.55 (1H, dd, J=4.8, 1.5 Hz), 7.78 (1H, dt, J=7.9, 1.5 Hz), 7.26 (1H, dd, J=7.9, 4.9 Hz), 7.16 (1H, d, J=9.6 Hz), 6.90 (1H, d, J=9.6 Hz), 5.24 (2H, s). 13C NMR (50 MHz, CDCl3) delta 158.63, 150.17, 149.62, 137.82, 136.64, 133.91, 132.17, 131.07, 123.54, 52.95, 19064-67-6

19064-67-6 6-Chloro-3-hydroxypyridazine 252828, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; Kohno, Yasushi; Adams, David Roger; Ando, Naoki; US2008/207902; (2008); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5096-73-1,6-Chloropyridazine-3-carboxylic acid,as a common compound, the synthetic route is as follows.,5096-73-1

Step 2: Methyl 6-chlorop yridazine-3 -carboxylate; To a suspension of -chloropyridazine-S-carboxylic acid (4.2 g, 26.5 mmol) in a mixture of toluene (100 mL) and DMF (2.5 mL, 31.8 mmol) was added oxalyl chloride (3.0 mL, 34 mmol). The mixture was stirred at room temperature for 1 h, and then concentrated to an oil. The oil was dissolved in dichloromethane (100 mL) and cooled to 0 C in an ice bath. To this solution was added methanol (20 mL) portionwise, maintaining the temperature of the reaction mixture below 10 C. After 1 h, the mixture was concentrated, and the resulting solid was suspended in diethyl ether and filtered. The solid was triturated with ethyl acetate and diethyl ether and the filtrate was evaporated to provide the title compound as a beige solid.

As the paragraph descriping shows that 5096-73-1 is playing an increasingly important role.

Reference£º
Patent; MERCK FROSST CANADA LTD.; WO2007/143823; (2007); A1;,
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50681-25-9, 4-Pyridazinecarboxylic Acid is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-(6-fluoroquinolin-2-yl)-2-methylaniline (100 mg, 0.40 mmol, 1 equiv) and pyridazine-4-carboxylic acid (73.8 mg, 0.59 mmol, 1.5 equiv) were dissolved in (0908) dichloromethane (5 mL) and diisopropylethylamine (102.5 mg, 0.79 mmol, 2 equiv) and HATU (226.1 mg, 0.59 mmol, 1.5 equiv) were added next. The resulting solution was stirred at room temperature overnight and quenched by the addition of 5 mL of water. Extraction with dichloromethane (2×5 ml) and elimination of volatiles under reduced pressure, afford a residue that was purified by preparative TLC with dichloromethane/methanol (25: 1) to afford the desired product as a white solid in 58% yield. LCMS (ES, m/z): [M+H]+ 359; -NMR (300 MHz, CO , ppm): 52.25 (s, 3H), 57.63-7.66 (m, 1H), 57.68-7.73 (m, 1H), 57.81-7.84 (m, 1H), 58.13-8.17 (m, 3H), 58.22-8.24 (m, 2H), 58.46-8.48 (d, 1H), 59.53-9.54 (d, 1H), 59.70 (s, 1H), 510.47 (s, 1H), 50681-25-9

The synthetic route of 50681-25-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; BECK, Hilary Plake; DILLON, Michael Patrick; GONZALEZ-LOPEZ, Marcos; RICO, Alice Chen; SUTTON, JR., James Clifford; (317 pag.)WO2019/18562; (2019); A1;,
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1121-79-5, 3-Chloro-6-methylpyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step A: A mixture of 3-chloro-6-methylpyridazine (516 mg, 4.0 mmol), NH4OH (30%, 3 mL) and copper(II) sulfate pentahydrate (26 mg, 0.2 mmol) was stirred at 120 C. for 40 h. The mixture was cooled to room temperature and partitioned between EtOAc and brine. The aqueous layer was extracted with EtOAc five times. The combined organics were dried over NaSO4, filtered, concentrated and purified by silica gel column chromatography (0-10% MeOH in CH2Cl2) to give 6-methylpyridazin-3-amine (160 mg, 37%) as a white solid. MS m/z 109.9 [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; PTC Therapeutics, Inc.; F. Hoffmann-La Roche AG; Woll, Matthew G.; Chen, Guangming; Choi, Soongyu; Dakka, Amal; Huang, Song; Karp, Gary Mitchell; Lee, Chang-Sun; Li, Chunshi; Narasimhan, Jana; Naryshkin, Nikolai; Paushkin, Sergey; Qi, Hongyan; Turpoff, Anthony A.; Weetall, Marla L.; Welch, Ellen; Yang, Tianle; Zhang, Nanjing; Zhang, Xiaoyan; Zhao, Xin; Pinard, Emmanuel; Ratni, Hasane; (317 pag.)US9617268; (2017); B2;,
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50681-25-9,50681-25-9, 4-Pyridazinecarboxylic Acid is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 7 7-Methyl-2-(4-pyridazinyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one Analogously to Example 6, starting from 6.0 g. (24 mmol) 5,6-diamino-3-methylindolin-2-one dihydrochloride and 3.6 g. (28.8 mmol) pyridazine-4-carboxylic acid, there is obtained the title compound. Purification takes place by column chromatography on silica gel (elution agent: methylene chloride/methanol 9:1 v/v). Yield: 0.15 g. (2.4% of theory); m.p. >340 C.

50681-25-9 4-Pyridazinecarboxylic Acid 2761046, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; Boehringer Mannheim GmbH; US4835280; (1989); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5788-58-9,4,5-Dibromopyridazin-3(2H)-one,as a common compound, the synthetic route is as follows.

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.

As the paragraph descriping shows that 5788-58-9 is playing an increasingly important role.

Reference£º
Patent; Nissan Chemical Industries Ltd.; US4978665; (1990); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2166-31-6,6-Phenylpyridazin-3(2H)-one,as a common compound, the synthetic route is as follows.

General procedure: To a solution of pyridazinone derivative [32-34] (0.5 mmol) in DMF (10 mL) was added 1-(chloromethyl) 3-nitrobenzene (0.52 mmol) and Cs2CO3 (0.55 mmol), the resulting reaction mixture was stirred at 40-50 C until no starting materials was detected by TLC (about 3 h). The solvent was removed under reduced pressure and the residue was dissolved in EtOAc (30 mL), washed with brine (3 10 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was dissolved in 95% ethanol (50 mL) containing 10 mmol acetic acid. Iron powder (2 mmol) was added and the resulting mixture was stirred for 5 h. After cooled to room temperature, the reaction mixture was filtered through celite and the filter cake was washed with 95% ethanol (3 x 15 mL). The combined ethanol layers were evaporated in vacuo and the residue was re-dissolved in ethyl acetate (30 mL). The organic layer was washed with brine (3 x 10 mL) and 2 M NaOH (10 mL) sequentially. The organic layer was dried over anhydrous Na2SO4, evaporated in vacuo to afford the crude 2-aminobenzyl-6-substituted-pyridazin-3(2H)-ones, which were used without further purification. To a stirred solution of 2-aminobenzyl-6-substituted-pyridazin-3(2H)-one and triphosgene (1 mmol) in dry dichloromethane (5 mL) was added triethylamine (2 mmol) under nitrogen atmosphere. A solution of the corresponding piperidine (1 mmol) in dichloromethane (5 mL) was added 5-10 min later and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane (15 mL) and washed with water (3 x 20 mL). The organic phases were separated, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography to afford the products., 2166-31-6

As the paragraph descriping shows that 2166-31-6 is playing an increasingly important role.

Reference£º
Article; Xing, Weiqiang; Fu, Yan; Shi, Zhangxing; Lu, Dong; Zhang, Haiyan; Hu, Youhong; European Journal of Medicinal Chemistry; vol. 63; (2013); p. 95 – 103;,
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