Heterocyclic Building Blocks-Pyridazine

1834-27-1, 6-Chloro-4-methylpyridazin-3(2H)-one is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 6-chloro-4-methylpyridazin-3-ol (Intermediate X17; 500 mg, 3.46mmol) in DCM (20.3 mL) and pyridine (1 mL, 3.46 mmol) was treated with (3,5-dimethoxyphenyl)boronic acid (1.26 g, 6.92 mmol), Cu(OAc)2 (1.26 g, 6.92 mmol), and pyridine 1-oxide (1 .32 g, 13.8 mmol). The resulting mixture was stirred open to the atmosphere overnight at ambient temperature. The reaction mixture was diluted with DCM (100 mL) and filtered. The filtrate was washed with water (2 x 30 mL), and the organics were dried over anhydrous Na2SO4(), filtered and concentrated under vacuum. The crude residue was precipitated from MeOH to cleanly afford the title compound (780 mg, 80%). MS (apci) m/z = 281.1 (M+H), 283.0 [(M+H)+2] (with Cl pattern).

1834-27-1, The synthetic route of 1834-27-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ARRAY BIOPHARMA, INC.; ANDREWS, Steven W.; BLAKE, James F.; COOK, Adam; GUNAWARDANA, Indrani W.; HUNT, Kevin W.; METCALF, Andrew T.; MORENO, David; REN, Li; TANG, Tony P.; (263 pag.)WO2017/70708; (2017); A1;,
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1632-74-2, 3,6-Dimethylpyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 17 4-(1-chloromethyl-1-methylethyl)-3,6-dimethylpyridazine A 23.9 g. portion of 2,2-dimethyl-1,3-propanediol, 88 ml. of water, 11.3 g. of 3,6-dimethylpyridazine, 3.6 g. of silver nitrate and 12.3 g. of concentrated sulfuric acid were combined at ambient temperature, and to the mixture was added 41.8 g. of ammonium persulfate dissolved in 68 ml. of water. The addition was dropwise over a period of only 15 minutes. The reaction temperature rose to 75, and the mixture was stirred at that temperature for 30 minutes. The reaction mixture was then worked up substantially as described in the examples above to obtain 1.2 g. of 4-(1-hydroxymethyl-1-methylethyl)-3,6-dimethylpyridazine.

1632-74-2, 1632-74-2 3,6-Dimethylpyridazine 527031, apyridazine compound, is more and more widely used in various fields.

Reference：
Patent; Eli Lilly and Company; US4791110; (1988); A;,
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Pyridazine | C4H4N2 – PubChem

5754-18-7, 1,2-Dihydro-4-methyl-3,6-pyridazinedione is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5754-18-7, 4-Methyl-1,2-dihydropyridazine-3,6-dione (9.48 g, 75.2 mmol) was suspended in phosphorus oxychloride (70 mL, 750 mmol) at ambient temperature under an atmosphere of N2 and then heated at gentle reflux for 4 h to give a golden yellow homogenous solution. The mixture was allowed to cool and excess phosphorous oxychloride was removed by vacuum distillation (14 mbar, 50-70 C). The residual viscous brown oil was slowly added to ice-cooled sat. NaHCO3 solution (200 mL) with vigorous stirring. The resulting heterogenous mixture was adjusted to pH 6 by the slow addition of solid NaHCO3 and then extracted with EtOAc (2 x 60 mL). The combined organic phase was washed with sat. NaCl solution (30 mL), dried (MgSO4) and evaporated to give the title compound (11.5 g, 70.8 mmol; 94%) as a yellow powder; mp 87-88C (from light petrol/diethyl ether); IR (KBr): 3054, 1567, 1434, 1351, 1326, 1145, 1121, 914, 720 cm-1. 1H NMR (200 MHz, CDCl3): delta 2.42 (3H, d, J = 1.0 Hz), 7.41 (1 H, q, J = 0.9 Hz); 13C NMR (50 MHz, CDCl3): 19.2 (CH3), 130.1 (CH-5), 140.7 (C-4), 155.6 (C-6), 157.3 (C-3); LRMS (EI) 162 ([M+]). Anal. calcd for C5H4Cl2N2: C, 36.84; H, 2.47; N, 17.19. Found: C, 36.93; H, 2.57; N, 17.48.

5754-18-7 1,2-Dihydro-4-methyl-3,6-pyridazinedione 79826, apyridazine compound, is more and more widely used in various fields.

Reference：
Article; Ochiai, Koji; Takita, Satoshi; Eiraku, Tomohiko; Kojima, Akihiko; Iwase, Kazuhiko; Kishi, Tetsuya; Fukuchi, Kazunori; Yasue, Tokutaro; Adams, David R.; Allcock, Robert W.; Jiang, Zhong; Kohno, Yasushi; Bioorganic and Medicinal Chemistry; vol. 20; 5; (2012); p. 1644 – 1658;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.36725-28-7,6-(4-Aminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one,as a common compound, the synthetic route is as follows.

Example 1 (Intermediate Compound) (R)-6-(4-hydrazino-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one A slight modification on the procedure described in J.Med.Chem. (1990), 33(10), 2870-2875 was used as follows. A solution of sodium nitrite (1.7 g) in water (12.5 ml) was added slowly at 0-5 C. to a solution of (R)-6-(4-aminophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one (5 g) in 1 M hydrochloric acid (75 ml). The resulting solution was stirred on ice bath for five minutes and then added slowly to a solution of tin(II)chloride dihydrate (17 g) in 1 M hydrochloric acid (150 ml) keeping the reaction temperature below 5 C. This solution was stirred on ice for forty minutes and then a solution of 50% NaOH (75 ml) was quickly added. The resulting mixture was stirred on ice bath until the temperature reached zero degrees Celsius. The crystals were filtered and washed with dilute ammonia. Yield: 5.0 g, 93%. HPLC: enantiomerically pure. 1H NMR (400 MHz, DMSO-d6): delta=1.04 (d, 3H, CH3), 2.17 (d, 1H, J=16 Hz), 2.60 (m, 1H), 3.29 (m, 1H), 4.04 (s, 2H, NH2), 6.77 (d, 2H, J=8 Hz), 7.09 (b, 1H, NH), 7.54 (d, 2H, J=8 Hz), 10.66 (s, 1H, NHCO)., 36725-28-7

As the paragraph descriping shows that 36725-28-7 is playing an increasingly important role.

Reference：
Patent; Pystynen, Jarmo; Pippuri, Aino; Luiro, Anne; Nore, Pentii; Backstrom, Reijo; Lonnberg, Kari; Haikala, Heimo; Levijoki, Jouko; Kaheinen, Petri; Kaivola, Juha; US2003/158200; (2003); A1;,
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108784-42-5, 6-Fluoropyridazin-3-amine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,108784-42-5

12. The starting material was prepared as follows: 6-amino-3-fluoropyridazine (1.15 mmoles; Footnote 6) and alpha’-chloro-alpha,alpha,alpha-trifluoro-m-xylene in the minimum of DMF were heated to 60 C. for 4 hours. Evaporation of the solvent and trituration of the residue with anhydrous ether gave 6-amino-3-fluoro-1-(3-trifluoromethylbenzyl)-pyridazinium chloride.

108784-42-5 6-Fluoropyridazin-3-amine 13719068, apyridazine compound, is more and more widely used in various fields.

Reference：
Patent; Imperial Chemical Industries plc; ICI Pharma; US5049558; (1991); A;,
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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.446273-59-2,3-Amino-4-bromo-6-chloropyridazine,as a common compound, the synthetic route is as follows.

4-Bromo-6-chloro-pyridazin-3-amine (5.2 g, 25 mmol) was combined with tetrakis(triphenylphosphine)palladium(0) (700 mg, 0.61 mmol) and DMF (50 mL). To the mixture was added dimethylzinc in heptane (50 mL, 50 mmol, 1.0 M) at room temperature. The mixture was heated at 50 C for 2 h then 70 C for 1 h. The mixture was cooled to 0 C and excess reagent was quenched by the addition of H20. The mixture was filtered over Celite and concentrated. The residue was chromatographed on silica gel, eluting with 0-10% MeOH in CH2C12. MS m/z 144.2, 146.2 [M+H]+.

446273-59-2, As the paragraph descriping shows that 446273-59-2 is playing an increasingly important role.

Reference：
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1352925-63-3,Ethyl 4,6-dihydroxypyridazine-3-carboxylate,as a common compound, the synthetic route is as follows.

1352925-63-3, To a solution of ethyl 4,6-dihydroxypyridazine-3-carboxylate (2.1 g, 11.40 mmol) in 40 ml NH3-CH3OH was held at room temperature with stirring on for 20h under N2. The solvents were removed in vacuo, and the residue was used to next step directly. m/z calcd for[C5H5N303]+ [M+H]+: 156.0; found: 156.0.

1352925-63-3 Ethyl 4,6-dihydroxypyridazine-3-carboxylate 69007765, apyridazine compound, is more and more widely used in various fields.

Reference：
Patent; GALECTO BIOTECH AB; BRIMERT, Thomas; JOHNSSON, Richard; LEFFLER, Hakon; NILSSON, Ulf; ZETTERBERG, Fredrik; (284 pag.)WO2016/120403; (2016); 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.29049-45-4,6-Chloropyridazin-4-amine,as a common compound, the synthetic route is as follows.

Synthesis of 5-bromo-3-chloropyridazine. To a solution 6-chloropyridazin-4-amine (2 g, 15 mmol), t-BuONO (2.4 g, 23 mmol) in MeCN (40 mL) was added CuBr2 (5 g, 23 mmol) at 0 C. The resulting mixture was stirred at RT for 16 h and then concentrated in vacuo. The mixture was diluted with EtOAc (50 mL) and added H2O (50 mL). After filtered through celite, the filtrate was extracted with EtOAc (50 mL*3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give the crude product which was purified by silica gel chromatography (PE/EA=20/1) to give 5-bromo-3-chloropyridazine (1.32 g, yield: 43%) as a brown oil. ESI-MS [M+H]+: 192.8, 194.8., 29049-45-4

29049-45-4 6-Chloropyridazin-4-amine 14099144, apyridazine compound, is more and more widely used in various fields.

Reference：
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
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Pyridazine | C4H4N2 – PubChem

108784-42-5, 6-Fluoropyridazin-3-amine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6-Fiuoro-pyridazin-3-ylamine [108784-42-5] (10 g, 89 mmol) was combined with a 50% (wjv)aqueous solution of chloroacetaldehyde [107-20-0] (23 ml, 177 mmol) inn-butanol (150 ml) and stirred at reflux for 1h. The cooled reaction solution was reduced in volume and diluted with diethylether to precipitate a brown solid, which was collected by filtration, to yield 12.0 g. LRMS (ESI) mjz138.0 [(M+H)J+, calc’d for CGH4FN3: 137.12.

108784-42-5, The synthetic route of 108784-42-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; LEXICON PHARMACEUTICALS, INC.; BI, Yingzhi; CARSON, Kenneth Gordon; CIANCHETTA, Giovanni; GREEN, Michael Alan; KUMI, Godwin; LIANG, Zhi; LIU, Ying Jade; MAIN, Alan; ZHANG, Yulian; ZIPP, Glenn Gregory; WO2013/134219; (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.33097-39-1,3,6-Difluoropyridazine,as a common compound, the synthetic route is as follows.

(1) A mixture of 3,6-difluoropyridazine (7.8 g) and 25 ml of concentrated ammonium hydroxide solution is heated in a sealed tube for 2 hours at 70 C. After cooling, the crystals separated are filtered and washed with water to give 4 g of 3-amino-6-fluoropyridazine. NMR spectrum (d6 -DMSO)delta: 6.23 (2H, br. s), 7-7.2 (2H, m).

33097-39-1, As the paragraph descriping shows that 33097-39-1 is playing an increasingly important role.

Reference：
Patent; Takeda Chemical Industries, Ltd.; US4864022; (1989); A;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem